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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 trifluoroacetone, which is applied in the preparation of carbonyl compounds, organic compounds/hydrides/coordination complexes, physical/chemical process catalysts, etc., can solve the problems of high flammability and mutagenicity of vinyl ethers, low storage capacity of trifluoroacetylated enamine, and high flammability of vinyl ethers

Inactive Publication Date: 2017-05-18
LONZA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent describes a new method for making 4-alkoxy-1,1,1-trifluorobut-3-en-2-ones without generating hydrogen chloride. The method produces only minimal amounts of byproducts, allowing for the use of non-HCl-resistant reactors. This method is also more cost-effective than previous methods due to its simplified procedure. The technical effects of this patent are improved efficiency, reduced waste, and lower costs for the production of important chemical intermediates.

Problems solved by technology

This route has disadvantages for the large scale production of 6-trifluoromethylpyridine-3-carboxylic acid derivatives, because ethylvinylether is highly flammable and therefore difficult to handle, and because the trifluoroacetylated enolether and the trifluoroacetylated enamine intermediates are unstable and cannot be stored for a longer time.
A disadvantage of this method is the formation of hydrogen chloride, which is corrosive and could lead to a product of low storability.
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
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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
Comparison scheme
Effect test

example 1

[0074]A mixture of 1,1,1-trifluoroacetone (0.80 ml, 8.93 mmol), triethylorthoformate (2.23 ml, 13.0 mmol) and acetic anhydride (2.53 ml, 27.0 mmol) was stirred in a closed vial at 140° C. for 16 h.

[0075]Analysis of a sample by 1H NMR (CDCl3) indicated formation of compound of formula (1) in 65% yield with respect to 1,1,1-trifluoroacetone used.

examples 2 to 5

[0076]Examples 2 to 5 were done in the same way as example 1, with any differences as given in Table 1.

TABLE 1MolarRatioExam-HC(OEt)3TriFAAc2O(II) / TriFA / TempTimeyieldple[mmol][mmol][mmol](IV)[° C.][h][%]2184.5274 / 1 / 6140104132.671.3442 / 1 / 3120121547.073.5710.72 / 1 / 3130213756.682.2313.43 / 1 / 61302151

example 6

[0077]A mixture of 1,1,1-trifluoroacetone (0.20 ml, 2.2 mmol), trimethylorthoformate (1.0 ml, 9.1 mmol), and acetic anhydride (1.6 ml, 16.9 mmol) was stirred in a closed vial at 140° C. for 16 h. Analysis of a sample by 1H NMR (CDCl3) indicated formation of compound of formula (2) in 78% yield with respect to trifluoroacetone used.

[0078]1H NMR (CDCl3, 400 MHz) delta=3.88 (s, 3H), 5.87 (d, J=12 Hz, 1H), 7.94 (d, J=12 Hz, 1H).

[0079]19F NMR (CDCl3) delta=78.08 ppm.

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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

[0001]The invention discloses a method for the preparation of 4-alkoxy-1,1,1-trifluorobut-3-en-2-ones from 1,1,1-trifluoroacetone.BACKGROUND OF THE INVENTION[0002]4-Alkoxy and 4-aryloxy-1,1,1-trifluorobut-3-en-2-ones of formula (I) are important synthetic intermediates for the preparation of fluorinated heterocycles.[0003]2-Trifluoromethylpyridines and 6-trifluoromethylpyridine-3-carboxylic acid derivatives are intermediates for the preparation of biologically active compounds. For instance, WO 00 / 39094 A1 discloses trifluoromethylpyridine as herbicides, WO 2006 / 059103 A2 discloses trifluoromethylpyridines as intermediates in the production of pharmaceutical, chemical and agro-chemical products, WO 2008 / 013414 A1 discloses trifluoromethylpyridines as vanilloid receptor antagonists and WO 2012 / 061926 A1 describes trifluoromethylpyridines as calcium channel blockers.[0004]WO 2005 / 026149 A, DE 24 29 674 A and EP 51 209 A disclose certain precursors used in instant invention.[0005]The c...

Claims

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Application Information

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IPC IPC(8): C07C45/70
CPCC07C45/70C07C49/255B01J31/0232
Inventor ZARAGOZA DOERWALD, FLORENCIOTAESCHLER, CHRISTOPH
Owner LONZA LTD