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Selective reduction method of ketone group in phenolcarboxylic acid ester

A carboxylic acid phenol ester and selective technology, which is applied in the field of selective reduction, can solve the problems of hidden safety hazards in the use of hydrogen, expensive palladium carbon, etc., and achieve the effects of mild reaction conditions, simple operation, and high yield

Inactive Publication Date: 2009-12-23
CHINA RESOURCES SAIKE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In view of the high price of palladium carbon and the potential safety hazards in the industrial use of hydrogen, the development of a cheaper and safer reduction method is of great significance for both theoretical research and industrial production

Method used

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  • Selective reduction method of ketone group in phenolcarboxylic acid ester
  • Selective reduction method of ketone group in phenolcarboxylic acid ester
  • Selective reduction method of ketone group in phenolcarboxylic acid ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Dissolve 30g of 3,5-diacetoxyacetophenone in 80ml of tetrahydrofuran, cool to -15°C, slowly add a tetrahydrofuran solution of zinc borohydride (prepared from sodium borohydride and anhydrous zinc chloride), and complete the addition , stirred at -15°C for 24 hours, evaporated the reaction solution to dryness, added 5% sodium hydroxide solution until the pH value was strongly alkaline, extracted twice with 100ml of dichloromethane, washed the combined extracts once with water, dried over magnesium sulfate, and filtered , and the mother liquor was evaporated to dryness to obtain 1-(1-hydroxyethyl)-3,5-diacetoxybenzene as a brownish-yellow liquid with a yield of 70%.

Embodiment 2

[0022] 20g of 2-methyl-3,5-diacetoxyacetophenone in 80ml of tetrahydrofuran, cooled to -15°C, slowly added the tetrahydrofuran solution of zinc borohydride, after the addition was completed, stirred at -15°C for 28 hours, and the reaction The liquid was evaporated to dryness, 5% sodium hydroxide solution was added until the pH value was strongly alkaline, extracted twice with 100 ml of dichloromethane, the combined extracts were washed once with water, dried over magnesium sulfate, filtered, and the mother liquor was evaporated to dryness to obtain the corresponding alcohol, which was collected rate of 65%.

Embodiment 3

[0024] Add 30g of 3,5-diacetoxyacetophenone solvent to 80ml of dioxane, cool to -15°C, slowly add the tetrahydrofuran solution of zinc borohydride, after the addition is complete, stir at -15°C for 24 hours, distill the reaction solution to dry, add 5% sodium hydroxide solution until the pH value is strongly alkaline, extract twice with 100ml of dichloromethane, wash the combined extracts once, dry over magnesium sulfate, filter, and evaporate the mother liquor to dryness to obtain 1-(1-hydroxyethyl Base)-3,5-diacetoxybenzene, brown liquid, yield 75%.

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Abstract

The invention relates to a selective reduction method of ketone group in phenolcarboxylic acid ester, comprising the following steps: dissolving ketone in anhydrous ether solvent, adding boron hydride in a molar ratio of 1-1.5 at 0 to 60 DEG C, performing a reaction at 0 to -60 DEG C for 24-36h, and treating the reaction solution to obtain the corresponding alcohols.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a selective reduction method for ketone groups in carboxylic acid phenol esters. Background technique [0002] In the process of drug synthesis, the problem of selective reduction of ketone groups in ester molecules is usually encountered. The current common solution is to selectively reduce ketone groups by hydrogen under the catalysis of palladium carbon. In view of the high price of palladium carbon and the potential safety hazards in the industrial use of hydrogen, the development of a cheaper and safer reduction method is of great significance for both theoretical research and industrial production. [0003] We found in 3,5-diacetoxystyrene, an important intermediate in the synthesis of resveratrol, that for the ketone group in the structure of formula I [0004] [0005] where R 1 H, C1-C4 alkyl or OAc [0006] R 2 H, C1-C4 alkyl or OAc [0007] R 3 H, C1-C4 alkyl ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/29C07C69/18C07C69/21
Inventor 闫起强李志强崔蕾邹江杨琰
Owner CHINA RESOURCES SAIKE PHARMA
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