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WO2003078368A1 - Derive de tetraalkoxypropane asymetrique - Google Patents

Derive de tetraalkoxypropane asymetrique Download PDF

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Publication number
WO2003078368A1
WO2003078368A1 PCT/JP2003/001559 JP0301559W WO03078368A1 WO 2003078368 A1 WO2003078368 A1 WO 2003078368A1 JP 0301559 W JP0301559 W JP 0301559W WO 03078368 A1 WO03078368 A1 WO 03078368A1
Authority
WO
WIPO (PCT)
Prior art keywords
asymmetric
mol
tetraalkoxypropane
propane
iso
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/JP2003/001559
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English (en)
Japanese (ja)
Inventor
Shinya Mita
Masahiro Murotani
Hiroaki Obata
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.)
Nippon Carbide Industries Co Inc
Original Assignee
Nippon Carbide Industries Co Inc
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 Nippon Carbide Industries Co Inc filed Critical Nippon Carbide Industries Co Inc
Priority to AU2003211987A priority Critical patent/AU2003211987A1/en
Publication of WO2003078368A1 publication Critical patent/WO2003078368A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/30—Compounds having groups
    • C07C43/303—Compounds having groups having acetal carbon atoms bound to acyclic carbon atoms

Definitions

  • the present invention relates to a novel asymmetric tetraalkoxypropane derivative, and more particularly, to a highly selective and highly reactive compound which is used as a raw material of, for example, virazole or pyrimidin, which is an intermediate for pharmaceutical and agricultural chemicals.
  • the present invention relates to asymmetric 1,3,3-trialkoxy_1-propoxypropane, a novel tetraalkoxypropane derivative useful as a bone skeletal forming agent.
  • Symmetric 1,1,3,3—tetraalkoxypropanes are known, for example, in US Pat. No. 5,049,098, 1,1,3,3-tetramethoxip mouthpan or 1,1,3,3— It describes the physical properties of tetraalkoxypropane. Further, as for asymmetric 1,1,3,3-tetraalkoxypropane, for example, in Non-Patent Document 1 below, 1,3,3—triethoxy-111 ( n -butoxy) propane or 1,3 , 3 — Triethoxy 1 _ (i S0 -butoxy) propane Physical properties are described.
  • the asymmetric tetraalkoxypropane derivatives of the present invention are: 1) 1,3,3-trimethoxy-1- (n-propoxy) propane; 2) 1,3,3-trimethoxy-1 -(iso-propoxy) propane, 3) 1,3,3-triethoxy-1- (n-propoxy) propane, 4) 1,3,3-triethoxy-1- (iso-propoxy) Regarding propane, see the literature and These compounds are new compounds, as they are not described in Chemical Abstract and, to the best of the present inventors, are not described in other documents. It is believed that there is.
  • Patent Document 1 and Non-Patent Document 1 describe methods for producing 1,1,3,3_tetramethoxypropane, 1,1,3,3_tetraethoxypropane, and the like. According to these documents, 1,1,3,3-tetramethoxy (or ethoxy) propane or the like, which is the target product, is synthesized from about 3 mol of orthoformate and 1 mol of a butyl ether corresponding to the ester. I have.
  • ethyl ethyl orthoformate and the corresponding ethyl vinyl ether are used, but ethyl butyl ether is a special flammable substance with a boiling point of 36 to 37 ° C. Use in large quantities was as difficult as with methyl vinyl ether.
  • the present inventors have proposed a highly selective and highly reactive 1,1,3,3-tetraalkoxypropane, which is useful as, for example, a raw material for pharmaceutical and agricultural chemical intermediates such as virazole and pyrimidine.
  • a highly selective and highly reactive 1,1,3,3-tetraalkoxypropane which is useful as, for example, a raw material for pharmaceutical and agricultural chemical intermediates such as virazole and pyrimidine.
  • a wide range of applications is possible, and as a compound having a high boiling point of 55 ° C. and a high industrial utility, a new asymmetric 1,3,3
  • the inventors have found that 3_trialkoxy-11-propoxypropane can be industrially produced, and have completed the present invention.
  • R 1 represents n- or iso-C 3 H 7 and R 2 represents CH 3 or C 2 H 5 )
  • novel asymmetric 1,3,3-trialkoxy compound of the present invention which is a novel compound
  • One propoxypropane is a compound represented by the above formula (I).
  • the asymmetric 1,3,3-trialkoxy-11-propoxylip bread according to the present invention can be produced, for example, according to the following reaction formula (II).
  • R 1 represents C 3 H 7 and R 2 represents CH 3 and C 2 H 5.
  • Specific examples of the method for synthesizing the compound of the present invention include the following methods. be able to.
  • Lewis such as anhydrous iron (III) chloride, boron trifluoride, hydrogen fluoride and mercuric chloride are used as a reaction catalyst.
  • the acid compound is preferably added in an amount of about 0.5 to 2.0 parts by weight, based on 100 parts by weight of the butyl ether, and, while stirring, for example, the orthoester of orthoformic acid is added in an amount of about 1.0 to 1.0 part per mole of vinyl ether. 3 mol is added, and aging reaction is performed at a temperature of, for example, about 0 ° C to 40 ° C.
  • the asymmetric 1,3,3-trialkoxy-11-propoxypropane which is the compound of the present invention, can be distilled off by subjecting the reaction mixture to distillation under reduced pressure.
  • Characteristic absorption body Roh cm- 1 null - 1 _ ⁇ .
  • this fraction was purified by a small high-speed rotary pan-type precision distillation apparatus to obtain 1.0 g of the above compound at 100% in terms of area percentage by gas chromatography (114 ° C, 6.7 ⁇ 10 ′′ 4 MPa) ).
  • the asymmetric 1,3,3-trialkoxy-1-propoxypropane according to the present invention is useful as a highly selective and highly reactive skeleton-forming agent used as a raw material for pyrazole-pyrimidine, which is an intermediate for pharmaceuticals and agrochemicals. It is.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un 1,3,3-trialkoxy-1-propoxypropane asymétrique représenté par la formule (I) dans laquelle R1 représente C3H7 et R2 représente CH3 ou C2H5. Il s'agit d'un composé utilisé, par exemple, en tant que matière pour le pyrazole, la pyrimidine, et autres substances semblables, qui sont des intermédiaires pour médicaments et produits chimiques agricoles.
PCT/JP2003/001559 2002-03-20 2003-02-14 Derive de tetraalkoxypropane asymetrique Ceased WO2003078368A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003211987A AU2003211987A1 (en) 2002-03-20 2003-02-14 Asymmetric tetraalkoxypropane derivative

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2002-77412 2002-03-20
JP2002077412A JP2005298341A (ja) 2002-03-20 2002-03-20 新規で非対称なテトラアルコキシプロパン誘導体

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US10/892,830 Continuation US8017733B2 (en) 2002-01-18 2004-07-16 Polyalkylene polymer compounds and uses thereof

Publications (1)

Publication Number Publication Date
WO2003078368A1 true WO2003078368A1 (fr) 2003-09-25

Family

ID=28035508

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2003/001559 Ceased WO2003078368A1 (fr) 2002-03-20 2003-02-14 Derive de tetraalkoxypropane asymetrique

Country Status (3)

Country Link
JP (1) JP2005298341A (fr)
AU (1) AU2003211987A1 (fr)
WO (1) WO2003078368A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1607381A4 (fr) * 2003-03-26 2006-09-13 Nippon Carbide Kogyo Kk Procede de production de tetra-alcoxypropane et derives de ce compose

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4410733A (en) * 1981-02-21 1983-10-18 Basf Aktiengesellschaft Preparation of acetals of malonaldehyde

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4410733A (en) * 1981-02-21 1983-10-18 Basf Aktiengesellschaft Preparation of acetals of malonaldehyde

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BREDERECK HELLMUT ET AL.: "Formamide reactions. VIII. A new pyrimidine synthesis", CHEM. BER., vol. 90, 1957, pages 942 - 952, XP002969967 *
KOBAYASHI EIJI: "Several reactions with alkyl vinyl ethers and their derivatives. I. Syntheses of 1,1,3,3-tetraalkoxy-propane", YAKUGAKU ZASSHI, vol. 82, 1962, pages 269 - 273, XP002969966 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1607381A4 (fr) * 2003-03-26 2006-09-13 Nippon Carbide Kogyo Kk Procede de production de tetra-alcoxypropane et derives de ce compose

Also Published As

Publication number Publication date
AU2003211987A1 (en) 2003-09-29
JP2005298341A (ja) 2005-10-27

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