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WO2006125550A1 - Procede de production de tetrahydropyrannes a partir de tetrahydropyrann-3-ones - Google Patents

Procede de production de tetrahydropyrannes a partir de tetrahydropyrann-3-ones Download PDF

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Publication number
WO2006125550A1
WO2006125550A1 PCT/EP2006/004607 EP2006004607W WO2006125550A1 WO 2006125550 A1 WO2006125550 A1 WO 2006125550A1 EP 2006004607 W EP2006004607 W EP 2006004607W WO 2006125550 A1 WO2006125550 A1 WO 2006125550A1
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WO
WIPO (PCT)
Prior art keywords
formula
compound
compounds
preparation
aldehyde
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2006/004607
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German (de)
English (en)
Inventor
Andreas Taugerbeck
Lars Lietzau
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Priority to KR1020077030176A priority Critical patent/KR101451979B1/ko
Priority to DE112006000985T priority patent/DE112006000985A5/de
Priority to CN2006800179551A priority patent/CN101180284B/zh
Priority to JP2008512732A priority patent/JP5148482B2/ja
Publication of WO2006125550A1 publication Critical patent/WO2006125550A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/30—Oxygen atoms, e.g. delta-lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D309/06—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/10—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to processes for the preparation of 2,5-disubstituted tetrahydropyrans from tetrahydropyran-3-ones as well as novel intermediates from these syntheses.
  • Tetrahydropyran rings as a component of chemical structures are an important feature of a wide range of classes of compounds.
  • the tetrahydropyrans already play an important role in the
  • Toxic mercury compounds are found in S.H. Kang et al. to synthesize a 2-methyl-5-phenyl-tetrahydropyran (Tetr. Lett., 1998, 39, 59-62).
  • C-nucleophiles a nucleophilic carbon atom
  • Heteroatoms are not directly linked, A 1 , A 2 , A 3 , A 4 , A 5 , A 6 1, 4-phenylene (which 0-4 times independently of each other by halogen, CH 3 , CF 3 , CHF 2 , CH 2 F 1 OCH 3 , OCHF 2 , OCF 3 may be substituted and wherein a ring CH may be substituted 0-2 times by N), cyclohexane-1, 4-diyl (CH 2 may be 0-2 independently of one another by O or S and / or 0-10 times by F), cyclobutane-1, 4-diyl, bicyclo [1.1.1] pentane-1,3-diyl, bicyclo [2.2.2] octane 1, 4-diyl, spiro [3.3] heptane-2,6-diyl, Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6, independently of one another,
  • the process according to the invention is based on the preparation and use of dihydropyran-3-one intermediate compounds of the formula II.
  • the preparation of compounds of the formula I is carried out in a process which comprises the reaction steps according to Scheme 1. - A -
  • a 1 , A 2 and A 3 are, if present, independent of each other
  • a 4 , A 5 and A 6 are, if present, independently of each other, optionally fluorinated 1, 4-phenylene, 1, 3-dioxane-2,5-diyl or 1, 4-cyclohexanediyl.
  • the process for the preparation of compounds of the formula I comprises a process step which is characterized in that a keto compound II and a metal-containing compound IM
  • n 1 or 2
  • M is a metal, a metal halide, a metal with another organic radical or any cation of an ion pair with
  • R 1 , R 2 , A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , a, b, c, d, e, f have the meaning as above for formula I.
  • the metal-containing compound of the formula III is a metallated
  • the process for the preparation of compounds of the formula I comprises a reaction step, which is characterized in that a compound of the formula IV by elimination of water to give compounds of the formula Va and / or Vb
  • R 1 , R 2 , A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , a, b , c, d, e, f, in the formulas Va and Vb have the same meaning as above for formula I.
  • the process is further characterized in that, in a reaction step, compounds of the formulas Va or Vb are converted by hydrogenation into compounds of the formula I.
  • organometallic compounds of the formula III which are characterized in that M is Li, Na, HaImg, when n is 1, where Hal is I, Br or Cl, or M equal to Mg when n equals 2.
  • the compounds of the formula I are prepared in a process which essentially converts the tetrahydropyranones of the formula II via a Wittig reaction with an ⁇ -alkoxyphosphorylide ( ⁇ -alkoxyphosphorane) and subsequent hydrolysis to formyltetrahydropyrans ( Scheme 2).
  • the Wittig reagent used is an enol ether synthon, such as the (alkoxymethyl) triphenylphosphonium halides, in particular commercially available Reagents, such.
  • B (methoxymethyl) triphenylphosphonium bromide or chloride.
  • the reaction conditions are analogous to those customary for Wittig reactions.
  • R 3 is an aryl radical and R 4 is an organic radical, to give an enol ether compound VII, hydrolyzed this to an aldehyde of formula VIII and then the aldehyde with a 1, 3-diol compound of the formula IX
  • Formula I is a group of the formula and where in
  • R 4 is preferably a simple, straight-chain or branched alkyl radical having 1-10 carbon atoms, in particular a methyl or ethyl radical.
  • aldehyde intermediates of the formula VIII are excellently suitable for the preparation of further products which can ultimately be converted into tetrahydropyran derivatives of the formula I.
  • these compounds are of particular interest for polar compounds having a dielectric anisotropy ⁇ > 0, since, when skillfully combined with other polar groups in the molecule, an enhanced dipole moment results in the direction of the longitudinal axis of the molecule. From these various reaction possibilities, the particular value of tetrahydropyranaldehydes results for the synthesis of different variants of the tetrahydropyran compounds according to formula I.
  • R 5 is an arbitrarily substituted alkyl radical, in particular a methyl group, a, b, c, R 1 , Z 1 , Z 2 , Z 3 , A 1 , A 2 and A 3 in the formulas VII and VIII have the same meaning as for formula I have.
  • aldehydes of the formula VIII are also suitable for the preparation of alkenyl chains by reaction with simple Wittig reagents such as phosphorylidene.
  • Optionally substituted alkenyl groups can also be attached to the tetrahydropyran ring using suitable Wittig reagents.
  • Alkenyl radicals are useful as chain end groups or as linkers between ring systems in mesogenic molecules.
  • the generated double bond in the vicinity of the tetrahydropyran ring can also be subsequently hydrogenated to a 1, 2-ethylene bridge, which in turn makes a wide range of mesogenic substances accessible.
  • the ethylene group formed can be used as a link between rings of the mesogenic molecule or as part of a terminal alkyl group. Preference is therefore also given to processes for the preparation of compounds of the formula I using aldehydes of the formula VIII or of aldehyde precursors of the formula VII
  • the aldehydes of formula VIII are extremely useful intermediates.
  • Preference is given to a process for the preparation of aldehydes of the formula VIII from keto compounds of the formula II.
  • Another object of the invention are serving as an intermediate new 3-keto-tetrahydropyrans having at least one
  • Novel compounds which are useful as intermediates are compounds of formula II
  • the ring A 1 is preferably an optionally mono- or polysubstituted with F 1, 4-phenylene, cyclohexane-1, 4-diyl or a tetrahydropyran-2,5-diyl.
  • Particularly preferred in this context are compounds of the formula II, for which A 1 , A 2 , A 3 is a mono- or polysubstituted with F 1, 4-phenylene.
  • compounds of the formula II in which Z 1 or Z 2 are each a single bond or -OCF 2 - are particularly preferred.
  • a further aspect of the invention is the preparation of tetrahydropyran-3-ones of the formula II as starting material for the others
  • MES stands for an organic molecule radical, in particular for mesogenic molecule radicals and parts thereof, ie for example also for a simple alkyl chain or analogously to formula II for the radical R 1 - [A 1 -Z 1 ] a - [A 2 -Z 2 ] b - [A 3 -Z 3 ] c -. Also in the reaction sequence may be several steps in one
  • the lactones as starting material are commercially available, or it may be the lactols and dihydropyrans z.
  • B. be prepared from aldehydes according to Scheme 4.
  • the aldehydes (MES-CHO) are reacted with Grignard compounds to give the alcohols from which the hemiacetals are obtained after hydrolysis of the acetal group to the aldehyde.
  • the molecular radical MES in the formulas given is a radical of the formula - [Z 3 -A 3 ] c - [Z 2 -A 2 ] b - [Z 1 -A 1 ] a -R 1 as defined below for the formula X.
  • a preferred process for the preparation of tetrahydropyranones of the formula II is therefore characterized in that a compound of the formula X is oxidized
  • the aldehyde can be derivatized to various compounds of formula I.
  • the aldehyde for example, is subsequently converted by a Wittig reaction into an alkenyl chain, which can optionally be further hydrogenated to the alkyl chain.
  • the aldehyde 5 is then reacted with 2-ethyl-1, 3-propanediol to dioxane 6.
  • 44.5 g (110 mmol) of the aldehyde 5 and 12.0 g (115 mmol) of the diol 6 are dissolved in 250 ml of toluene, treated with 400 mg of p-Toluolsulfonklamonohydrat and until complete conversion of the aldehyde (DC) on a water heated to reflux.
  • the cooled batch is washed three times with sat.
  • Washed sodium bicarbonate solution concentrated and passed through silica gel (toluene / heptane 7: 3, toluene, toluene / ethyl acetate 95: 5).
  • the product-containing fractions are concentrated and the residue recrystallized at -20 0 C from ethanol. Mp .: 88 0 C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyrane Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

Procédé de production de tétrahydropyrannes 2,5-disubstitués à partir de tétrahydropyrann-3-ones, et nouvelles étapes intermédiaires dérivées de ces synthèses.
PCT/EP2006/004607 2005-05-25 2006-05-16 Procede de production de tetrahydropyrannes a partir de tetrahydropyrann-3-ones Ceased WO2006125550A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
KR1020077030176A KR101451979B1 (ko) 2005-05-25 2006-05-16 테트라하이드로피란-3-온으로부터 테트라하이드로피란의제조 방법
DE112006000985T DE112006000985A5 (de) 2005-05-25 2006-05-16 Verfahren zur Herstellung von Tetrahydropyranen aus Tetrahydropyran-3-onen
CN2006800179551A CN101180284B (zh) 2005-05-25 2006-05-16 从四氢吡喃-3-酮制备四氢吡喃的方法
JP2008512732A JP5148482B2 (ja) 2005-05-25 2006-05-16 テトラヒドロピラン−３−オン類からテトラヒドロピラン類を調製する方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP05011320.8 2005-05-25
EP05011320 2005-05-25

Publications (1)

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WO2006125550A1 true WO2006125550A1 (fr) 2006-11-30

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PCT/EP2006/004607 Ceased WO2006125550A1 (fr) 2005-05-25 2006-05-16 Procede de production de tetrahydropyrannes a partir de tetrahydropyrann-3-ones

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JP (1) JP5148482B2 (fr)
KR (1) KR101451979B1 (fr)
CN (1) CN101180284B (fr)
DE (1) DE112006000985A5 (fr)
WO (1) WO2006125550A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7790247B2 (en) * 2006-10-04 2010-09-07 Merck Patent Gmbh Liquid-crystalline medium
US20150307804A1 (en) * 2012-12-07 2015-10-29 The Lubrizol Corporation Pyran Dispersants
WO2016185793A1 (fr) * 2015-05-20 2016-11-24 Jnc株式会社 Composition de cristaux liquides et élément d'affichage à cristaux liquides
US10174252B2 (en) 2015-02-24 2019-01-08 Jnc Corporation Liquid crystal composition and liquid crystal display device

Families Citing this family (6)

* Cited by examiner, † Cited by third party
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JP5135765B2 (ja) * 2005-11-15 2013-02-06 Ｊｎｃ株式会社 ラクトン環を含有する液晶性化合物、液晶組成物、および液晶表示素子
CN102718736B (zh) * 2012-06-07 2014-08-06 北京八亿时空液晶科技股份有限公司 一种吡喃类含氟化合物、制备方法及其用途
JP6435923B2 (ja) 2014-03-07 2018-12-12 Jnc株式会社 ジヒドロピラン化合物、液晶組成物および液晶表示素子
JP6627515B2 (ja) 2015-02-06 2020-01-08 Jnc株式会社 ３，６−ジヒドロ−２ｈ−ピランを有する誘電率異方性が負の液晶性化合物、液晶組成物および液晶表示素子
JP6489369B2 (ja) * 2015-06-23 2019-03-27 Dic株式会社 ジフルオロメチルエーテル骨格を有する化合物の製造方法及びその製造中間体化合物
JP2017190323A (ja) * 2016-04-08 2017-10-19 Jnc株式会社 テトラヒドロ−２ｈ−ピラン誘導体の製造方法

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WO2004048357A1 (fr) * 2002-11-27 2004-06-10 Merck Patent Gmbh Derives de tetrahydropyrane

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EP0117476A1 (fr) * 1983-02-28 1984-09-05 MERCK PATENT GmbH Tétrahydropyrannes
WO2004048357A1 (fr) * 2002-11-27 2004-06-10 Merck Patent Gmbh Derives de tetrahydropyrane

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7790247B2 (en) * 2006-10-04 2010-09-07 Merck Patent Gmbh Liquid-crystalline medium
US20150307804A1 (en) * 2012-12-07 2015-10-29 The Lubrizol Corporation Pyran Dispersants
US9695377B2 (en) * 2012-12-07 2017-07-04 The Lubrizol Corporation Pyran dispersants
US10174252B2 (en) 2015-02-24 2019-01-08 Jnc Corporation Liquid crystal composition and liquid crystal display device
WO2016185793A1 (fr) * 2015-05-20 2016-11-24 Jnc株式会社 Composition de cristaux liquides et élément d'affichage à cristaux liquides

Also Published As

Publication number Publication date
JP5148482B2 (ja) 2013-02-20
CN101180284A (zh) 2008-05-14
JP2008545671A (ja) 2008-12-18
DE112006000985A5 (de) 2008-04-03
KR20080019020A (ko) 2008-02-29
KR101451979B1 (ko) 2014-10-21
CN101180284B (zh) 2013-03-27

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