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Method for preparation of 4-alkoxy-1,1,1-trifluorobut-3-en-2- ones from 1,1,1-trifluoroacetone

A technology of trifluoroacetone and alkyl, applied in the field of preparing 4-alkoxy-1,1,1-trifluorobut-3-en-2-one, which can solve the problem of high flammability and mutagenicity problem, to achieve the effect of less cost

Inactive Publication Date: 2017-02-15
LONZA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A further disadvantage of this synthetic strategy for the large-scale production of 4-alkoxy-1,1,1-trifluorobut-3-en-2-ones is the high flammability and mutagenicity of vinyl ethers

Method used

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  • Method for preparation of 4-alkoxy-1,1,1-trifluorobut-3-en-2- ones from 1,1,1-trifluoroacetone

Examples

Experimental program
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Effect test

Embodiment 1

[0094] A mixture of 1,1,1-trifluoroacetone (0.80ml, 8.93mmol), triethyl orthoformate (2.23ml, 13.0mmol) and acetic anhydride (2.53ml, 27.0mmol) was stirred at 140°C in a closed vial , for 16 hours.

[0095] pass 1 H NMR (CDCl 3 ) analysis of a sample showed the formation of the compound of formula (1) in 65% yield relative to the 1,1,1-trifluoroacetone used.

[0096]

Embodiment 2-5

[0098] Table 1 Example HC(OEt) 3

Embodiment 6

[0100] A mixture of 1,1,1-trifluoroacetone (0.20ml, 2.2mmol), triethyl orthoformate (1.0ml, 9.1mmol) and acetic anhydride (1.6ml, 16.9mmol) was stirred at 140°C in a closed vial , for 16 hours. pass 1 H NMR (CDCl 3 ) analysis of a sample showed the formation of the compound of formula (2) in 78% yield relative to the trifluoroacetone used.

[0101]

[0102] 1 H NMR (CDCl 3 ,400MHz)δ=3.88(s,3H),5.87(d,J=12Hz,1H),7.94(d,J=12Hz,1H).

[0103] 19 F NMR (CDCl 3 )δ=78.08ppm.

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Abstract

The invention discloses a method for the preparation of 4-alkoxy-1,1,1-trifluorobut-3-en-2-ones from 1,1,1-trifluoroacetone.

Description

technical field [0001] The invention discloses a method for preparing 4-alkoxy-1,1,1-trifluorobut-3-en-2-one from 1,1,1-trifluoroacetone. Background technique [0002] 4-alkoxy-1,1,1-trifluorobut-3-en-2-one and 4-aryloxy-1,1,1-trifluorobut-3-ene-2 ​​of formula (I) -Kones are important synthetic intermediates for the preparation of fluorinated heterocycles. [0003] 2-Trifluoromethylpyridine and 6-trifluoromethylpyridine-3-carboxylic acid derivatives are intermediates for the preparation of biologically active compounds. For example, WO 00 / 39094 A1 discloses the use of trifluoromethylpyridine as a herbicide, WO 2006 / 059103 A2 discloses the use of trifluoromethylpyridine as an intermediate in the production of pharmaceuticals, chemicals and agrochemicals, WO 2008 / 013414 A1 discloses the use of trifluoromethylpyridines as capsaicin receptor antagonists and WO 2012 / 061926 A1 describes the use of trifluoromethylpyridines as calcium channel blockers. [0004] WO 2005 / 026149 A, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/70C07C49/255
CPCC07C45/70C07C49/255B01J31/0232
Inventor 弗洛伦西奥·萨拉戈萨杜尔瓦尔德克利斯多夫·塔施勒
Owner LONZA LTD
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