PL422237A1 - Derivative of thiophene and method for obtaining it - Google Patents
Derivative of thiophene and method for obtaining itInfo
- Publication number
- PL422237A1 PL422237A1 PL422237A PL42223717A PL422237A1 PL 422237 A1 PL422237 A1 PL 422237A1 PL 422237 A PL422237 A PL 422237A PL 42223717 A PL42223717 A PL 42223717A PL 422237 A1 PL422237 A1 PL 422237A1
- Authority
- PL
- Poland
- Prior art keywords
- environment
- reaction
- subjected
- reduction
- isolation
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 150000003577 thiophenes Chemical class 0.000 title abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 4
- 238000006722 reduction reaction Methods 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- 238000002955 isolation Methods 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 abstract 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000012429 reaction media Substances 0.000 abstract 2
- JVFWKWMSTLLUGZ-UHFFFAOYSA-N 4-(3-methylthiophen-2-yl)butan-2-ol Chemical compound CC(O)CCC=1SC=CC=1C JVFWKWMSTLLUGZ-UHFFFAOYSA-N 0.000 abstract 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 abstract 1
- LSSRGAPUBFMBRJ-UHFFFAOYSA-N C(C)(=O)OC(CCC=1SC(=CC=1C)CCCC)C Chemical compound C(C)(=O)OC(CCC=1SC(=CC=1C)CCCC)C LSSRGAPUBFMBRJ-UHFFFAOYSA-N 0.000 abstract 1
- AUWLPLYJNSYPMW-UHFFFAOYSA-N C(CCC)C1=C(C=C(S1)CCC(C)=O)C Chemical compound C(CCC)C1=C(C=C(S1)CCC(C)=O)C AUWLPLYJNSYPMW-UHFFFAOYSA-N 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 235000021419 vinegar Nutrition 0.000 abstract 1
- 239000000052 vinegar Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Przedmiotem zgłoszenia jest nowy związek, pochodna tiofenu, którą stanowi octan 3-(5-butylo-3-metylotiofen-2-ylo)-1-metylopropylu o wzorze 1. Zgłoszenie dotyczy także sposobu otrzymywania tego związku, który polega na tym, że 4-(3-metylotiofen-2-ylo)-butan-2-on poddaje się reakcji redukcji borowodorkiem sodu w środowisku metanolu, otrzymany w tej reakcji 4-(3-metylo-tiofen-2-ylo)-butan-2-ol, po wyodrębnieniu ze środowiska reakcji, poddaje się reakcji alkilowania metylowinyloketonem w obecności eteratu trifluorku boru w środowisku dichlorometanu, po czym otrzymany w tej reakcji 4-[3-metylo-5-(3-okso-butylo)tiofen-2-ylo]-butan-2-ol, po wyodrębnieniu ze środowiska reakcji, poddaje się redukcji roztworem wodnym hydrazyny w obecności wodorotlenku potasu w środowisku glikolu propylenowego, produkt redukcji, po oddestylowaniu nadmiaru wody i hydrazyny, oraz wydzieleniu się azotu, wyodrębnia się ze środowiska redukcji i poddaje estryfikacji bezwodnikiem octowym w obecności pirydyny w środowisku dichlorometanu, a produkt estryfikacji, po wyodrębnieniu ze środowiska, oczyszcza się chromatograficznie.The subject of the application is a new compound, a thiophene derivative, which is 3- (5-butyl-3-methylthiophen-2-yl) -1-methylpropyl acetate of formula 1. The application also relates to a method of obtaining this compound, which consists in that - (3-methylthiophen-2-yl) -butan-2-one is subjected to a reduction reaction with sodium borohydride in a methanol medium, obtained in this reaction 4- (3-methyl-thiophen-2-yl) -butan-2-ol, after isolation from the reaction medium, it is subjected to an alkylation reaction with methyl vinyl ketone in the presence of boron trifluoride etherate in a dichloromethane environment, followed by the 4- [3-methyl-5- (3-oxo-butyl) thiophen-2-yl] butane obtained in this reaction -2-ol, after isolation from the reaction medium, is subjected to reduction with an aqueous solution of hydrazine in the presence of potassium hydroxide in a propylene glycol environment, the reduction product, after distilling off the excess water and hydrazine, and the evolution of nitrogen, is extracted from the reduction environment and subjected to anhydrification with anhydride vinegar in the present of pyridine in a dichloromethane environment, and the esterification product, after isolation from the environment, is purified by chromatography.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL422237A PL236430B1 (en) | 2017-07-17 | 2017-07-17 | Derivative of thiophene and method for obtaining it |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL422237A PL236430B1 (en) | 2017-07-17 | 2017-07-17 | Derivative of thiophene and method for obtaining it |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL422237A1 true PL422237A1 (en) | 2019-01-28 |
| PL236430B1 PL236430B1 (en) | 2021-01-11 |
Family
ID=65033980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL422237A PL236430B1 (en) | 2017-07-17 | 2017-07-17 | Derivative of thiophene and method for obtaining it |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL236430B1 (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003053953A1 (en) * | 2001-12-19 | 2003-07-03 | Flexitral Inc. | Thiophene derivatives and their use as fragrants |
| PL412803A1 (en) * | 2015-06-22 | 2017-01-02 | Politechnika Łódzka | Derivative of thiophene and method for obtaining it |
-
2017
- 2017-07-17 PL PL422237A patent/PL236430B1/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003053953A1 (en) * | 2001-12-19 | 2003-07-03 | Flexitral Inc. | Thiophene derivatives and their use as fragrants |
| PL412803A1 (en) * | 2015-06-22 | 2017-01-02 | Politechnika Łódzka | Derivative of thiophene and method for obtaining it |
Also Published As
| Publication number | Publication date |
|---|---|
| PL236430B1 (en) | 2021-01-11 |
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