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Method for preparing perfluoroalkyl alkyl ketone compound

A technology for perfluoroalkyl alkyl ketones and compounds, which is applied in the field of preparing perfluoroalkyl alkyl ketone compounds, and can solve problems such as poor selectivity, poor reaction selectivity, and low yield

Inactive Publication Date: 2015-02-25
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to its wide range of uses, the synthesis of perfluoroalkyl alkyl ketones has attracted more and more attention from scientists. The synthesis methods mainly include: (1) hydrocarbyl metal reagents (Grignard reagents, hydrocarbyl lithium, etc.) and trifluoroacetic acid, ester Or salt reaction (JACS, 1956, 78, 2268-2270), which is a method often used by researchers, but it uses metal organic reagents such as Grignard reagents and hydrocarbyl lithium as reaction substrates, and requires high operating conditions , and the reaction selectivity is poor, the yield is not high
(2) Under the promotion of sodium methoxide, Claisen acylation and condensation of ketones and trifluoroacetates to generate β-ketones followed by cracking (JACS, 1953, 75, 2059). This method has poor selectivity and yield low rate
(3) Reaction of acid chlorides with trifluoroacetic anhydride (Tetrahedron, 1995, 51:2573-2584), which is also a method currently used, but requires a large excess of trifluoroacetic anhydride and pyridine
(4) Hydrolytic decarboxylation after condensation of α-H-containing carboxylic acid / ester with perfluorocarboxylate (JACS, 1956, 78: 4053-4057; JOC, 2008: 9476-9478), the yield of this method is not high , and requires a low temperature of -65°C
[0003] In summary, although there are many reports on the synthesis methods of perfluoroalkyl alkyl ketones, these methods have problems such as poor selectivity, low yield, harsh reaction conditions, etc., and cannot meet the actual needs well.

Method used

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  • Method for preparing perfluoroalkyl alkyl ketone compound
  • Method for preparing perfluoroalkyl alkyl ketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1 Preparation of 1,1,1-trifluoro-4-phenyl-2-butanone (compound 1) by NaH-THF system

[0044] After vacuuming the 50ml Schlenk bottle N 2 Replace three times, add NaH 0.12g (5mmol), add anhydrous THF 10ml, stir at room temperature, the system is gray homogeneous, dropwise add ethyl trifluoroacetate 0.8g (5.6mmol), the reaction bottle system turns into white homogeneous. After evacuating another Schlenk bottle, N 2 Replacement, add 1g (4.8mmol) of 1,3-diphenyl-1-propanone, add 10ml of anhydrous THF to dissolve, it becomes a colorless transparent liquid, slowly drop the liquid into the above-mentioned solution containing trifluoro In the reaction bottle of ethyl acetate, it was slowly raised to room temperature, gas phase detection, and the reaction ended after 3 hours. Add the reacted liquid dropwise to ice water with a dropper under stirring, add 1M HCl to neutralize it, add ethyl acetate for extraction (10ml×3 times), combine the organic phases, add anhydrous ...

Embodiment 2

[0045] Example 2 Preparation of 1,1,1-trifluoro-3-(4-chloro-phenoxy)-2-propanone (compound 2) by KH-THF system

[0046] Except that the 1,3-diphenyl-1-propanone in Example 1 was replaced by the same mole of 1-phenyl-2-(4-chloro-phenoxy)-1-ethanone and NaH was replaced by the same mole Except for the moles of KH, the same method as in Example 1 was followed to obtain 1.13 g of the product 1,1,1-trifluoro-3-(4-chloro-phenoxy)-2-propanone, with a yield of 97%.

Embodiment 3

[0047] Example 3 Preparation of 1,1,1-trifluoro-2-cyclopentyl-2-ethanone (compound 3) by NaH-THF system

[0048] Except that the 1,3-diphenyl-1-propanone in Example 1 is replaced by the same mole of phenylcyclopentyl ketone, the same method as in Example 1 is carried out to obtain the product 1,1,1- Trifluoro-2-cyclopentyl-2-ethanone 0.45g, yield 56%.

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Abstract

The invention relates to a method for preparing a perfluoroalkyl alkyl ketone compound. A structural formula of the perfluoroalkyl alkyl ketone compound is shown in a formula I, and is characterized in that a compound II and perfluorinated carboxylic ester are used as raw materials, and the compound II and perfluorinated carboxylic ester react in an anhydrous solvent under the action of alkali according to a reaction formula as shown in the specification so as to obtain the perfluoroalkyl alkyl ketone compound shown in the structural formula I.

Description

technical field [0001] The present invention relates to a method for preparing perfluoroalkyl alkyl ketone compounds. Background technique [0002] Perfluoroalkyl alkyl ketones have potential biological and pharmacological activities and are broad biological enzyme inhibitors (J Mol Model. 2010, 1753–1764; Bioorganic & Medicinal Chemistry. 2008, 4652–4660). Moreover, it is an important chemical synthesis intermediate (Organ.Lett.2009,1887-1890; Eur.J.Org.Chem.2004,749.], widely used in drugs, polymer materials, liquid crystal materials, fluorescent probes Synthesis of etc. Due to its wide range of uses, the synthesis of perfluoroalkyl alkyl ketones has attracted more and more attention from scientists. The synthesis methods mainly include: (1) hydrocarbyl metal reagents (Grignard reagents, hydrocarbyl lithium, etc.) Fluoroacetic acid, ester or salt reaction (JACS, 1956, 78, 2268-2270), which is a method often used by researchers, but it uses metal organic reagents such as G...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B37/04C07C45/54C07C49/233C07C49/255C07C49/327C07C49/167C07C69/76C07C67/333C07D307/46C07D333/22
Inventor 周宇涵曲景平杨冬梅薛娜
Owner DALIAN UNIV OF TECH