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Preparation method of aromatic cyclopropyl ketone compound and purpose

A technology for cyclopropyl ethyl ketone and compounds, which is applied in the direction of condensation preparation of carbonyl compounds, organic chemistry, etc., can solve the problems of difficult post-processing, toxicity of reaction solvents, serious environmental pollution, etc., and achieves high industrial application, economic value, and low price. , the effect of reducing pollution

Active Publication Date: 2014-07-16
ZHEJIANG JIUZHOU PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The object of the present invention is to adopt strong base, replace isopropyl magnesium chloride, overcome prior art cyclopropyl nitrile environmental pollution is serious, easily produces cyanide; Oxygen conditions are strict, the reaction solvent is highly toxic, and the disadvantages of high cost provide a more economical and convenient synthetic method for the preparation of aromatic cyclopropyl ethyl ketones

Method used

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  • Preparation method of aromatic cyclopropyl ketone compound and purpose
  • Preparation method of aromatic cyclopropyl ketone compound and purpose
  • Preparation method of aromatic cyclopropyl ketone compound and purpose

Examples

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Embodiment 1

[0024] Example 1: Preparation of 1-cyclopropyl-2-(2-fluorophenyl)ethanone

[0025] Add 2-(2-fluorophenyl)acetic acid (10.0g, 64.9mmol) into 30ml of anhydrous tetrahydrofuran, add dropwise to the cloudy solution containing sodium hydride (3.9g, 97.4mmol) and 140mL of tetrahydrofuran at 10°C, drop After completion, the reaction mixture was heated to 30°C and stirred for 1 hour, then a mixed solution of methylcyclopropylcarboxylic acid (7.0ml, 69.8mmol, 1.07eq) and 30ml of anhydrous tetrahydrofuran was added dropwise, and stirring was continued for 10 hours after the dropwise addition was completed. After the reaction is completed, add ammonium chloride solution dropwise to quench excess sodium hydride, separate liquids, extract, concentrate the organic phase, and distill the resulting liquid under reduced pressure to obtain 1-cyclopropyl-2-(2-fluorophenyl)ethanone 10.8 g, yield 93.5%.

[0026] 1 H NMR (CDCl 3 , Me 4 Si) δ0.86-0.90 (m, 2H), 1.05-1.08 (m, 2H), 1.97-2.02 (m, 1H...

Embodiment 2

[0027] Example 2: Preparation of 1-cyclopropyl-2-(2-fluorophenyl)ethanone

[0028] Add 2-(2-fluorophenyl)acetic acid (10.0g, 64.9mmol) into 30ml of anhydrous methanol, dropwise add sodium methoxide (4.6g, 85mmol) and 100ml of methanol into the turbid solution at 10°C, dropwise The reaction mixture was heated to 30°C and stirred for 1 hour, then a mixture of methylcyclopropylcarboxylic acid (7.0ml, 69.8mmol, 1.07eq) and 30ml of methanol was added dropwise, and stirring was continued for 10 hours after the completion of the dropwise addition. Add ammonium chloride solution to quench excess sodium methoxide, separate liquids, extract, and concentrate the organic phase. The resulting liquid is distilled under reduced pressure to obtain 9.4 g of 1-cyclopropyl-2-(2-fluorophenyl)ethanone. The rate is 81.3%.

Embodiment 3

[0029] Embodiment 3: Preparation of 1-cyclopropyl-2-(3-tolyl)ethanone

[0030] Take by weighing 2-(3-toluene) acetic acid 10.0g, sodium hydride 4.0g, operate in the same way according to the method of embodiment 1, obtain 1-cyclopropyl-2-(3-toluene) ethyl ketone 9.18g, yield is 79.2%.

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Abstract

The invention relates to the technical field of carbocyclic ring chemical technology, concretely relates to a preparation method of an aromatic cyclopropyl ketone compound and its purpose. The preparation method comprises the following steps: mixing a compound in a formula (a) with alkali and stirring, reacting with a compound in a formula (b) to obtain the aromatic cyclopropyl ketone compound which is a compound in a formula (c), the compound in a formula (c) is used for preparing a tetrahydrothienopyridine derivative, when R1 is 2 position fluorine atom, the compound in the formula (c) is an important intermediate for preparing prasugrel. The structural formula of the compound is shown as the following: wherein, R1 is halogen or C1-C4 alkyl; R2 is C1-C4 alkyl.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to the technical field of carbocyclic chemistry. Background technique [0002] Aromatic cyclopropyl ethyl ketones are important intermediates for the synthesis of tetrahydrothienopyridine derivatives, among which the more important tetrahydrothienopyridine derivatives are prasugrel, whose chemical name is 2-acetoxy-5- (a-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine, whose structural formula is shown in the compound of formula (1) below, is produced by Japan Sankyo (sankyo) and Lilly of the United States jointly developed a drug for the treatment of blood clots. The method for synthesizing tetrahydrothienopyridine derivatives from aromatic cyclopropyl ethyl ketones has been recorded in patent CN101177430 or patent CN101250193, and the specific published route is as follows: [0003] [0004] The synthesis of aromatic cyclopropyl ethyl ketones can r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/567C07C49/563C07C45/48C07D495/04
Inventor 李涛高红军车大庆
Owner ZHEJIANG JIUZHOU PHARM CO LTD
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