Synthesis method of benzylisofuryl alcohol

A synthetic method, the technology of benzfuranol, which is applied in the field of synthesis of pesticide intermediates, can solve the problems of unsatisfactory overall yield, low yield of second-step formylation, low selectivity, etc.

Pending Publication Date: 2022-08-05
YANCHENG TEACHERS UNIV
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  • Summary
  • Abstract
  • Description
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Problems solved by technology

Wherein the yield of the second step formylation is low, the

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] (1) 100 mL of tetrahydrofuran and 55 mL of lithium diisopropylamide solution (2.0 mol / L tetrahydrofuran solution) were added to a 250 mL three-necked flask at -60°C. To this solution, 5.8 g of acetone was slowly added, and after reacting for one hour, the temperature was further lowered to -60°C, and then 7.2 g of 3-oxetanone was added. After the addition was complete, the mixture was stirred at room temperature for 6 hours. After the reaction was completed, the reaction was quenched with ammonium chloride solution, the aqueous layer was extracted twice with 200 mL of ethyl acetate, the organic phases were combined, and the organic solvent was distilled off under reduced pressure to obtain 11.2 g of the product with a content of 97.3% and a yield of 86%.

[0016] (2) The product obtained after the completion of the reaction in step (1) and 100 mL of dichloromethane were charged into a 250 mL three-necked flask. At room temperature, 2 g of trifluoroacetic acid was added...

Embodiment 2

[0022] (1) 100 mL of diethyl ether and 55 mL of lithium diisopropylamide solution (2.0 mol / L tetrahydrofuran solution) were added to a 250 mL three-necked flask at -60°C. To the solution, 5.8 g of acetone was slowly added, and after reacting for one hour, the temperature was continued to -60° C., and then 7.2 g of 3-oxetanone was added. After the addition was complete, the mixture was stirred at room temperature for 5 hours. After the reaction was completed, the reaction was quenched with ammonium chloride solution, the aqueous layer was extracted twice with 200 mL of ethyl acetate, the organic phases were combined, and the organic solvent was distilled off under reduced pressure to obtain 11.5 g of the product with a content of 97.6% and a yield of 88%.

[0023] (2) The product obtained after the completion of the reaction in step (1) and 100 mL of dichloromethane were charged into a 250 mL three-necked flask. At room temperature, 1.5 g of boron trifluoride ether was added, ...

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Abstract

The invention relates to a synthesis technology of an insecticidal pesticide intermediate, and in particular relates to a synthesis method of a benzfuryl alcohol compound. The preparation method is characterized by comprising the following steps: (1) deprotonating acetone at the temperature of-50 to-70 DEG C, and reacting the deprotonated acetone with oxetanone to obtain a 3-oxetanol derivative; (2) carrying out ring-opening reaction on the product obtained in the step (1) under the action of acid to obtain 2-methyl-3-furanol; (3) protecting hydroxyl in the product obtained in the step (2) by using chlorosilane; (4) brominating methyl in the product obtained in the step (3); (5) carrying out substitution reaction on the product obtained in the step (4) and phenyl lithium or phenyl magnesium bromide to obtain a benzfuryl silyl ether compound; and (6) carrying out silicon-based deprotection on the benzfuryl silyl ether obtained in the step (5) by using fluoride to obtain the benzfuryl alcohol compound. The synthesis method of the benzyl furofuryl alcohol is convenient to operate, the raw materials are simple and easy to obtain, and the overall yield is obviously improved compared with the prior art.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a synthesis technology of a pesticide intermediate. Background technique [0002] Resmethrin is a good household hygienic insecticide, and because of its extremely low toxicity, it also has a wide range of uses in grain storage. As early as 1975, the Food and Agriculture Organization of the United Nations and the World Health Organization approved the drug to be used directly for raw and finished grains (such as rice, flour, etc.) to control food pests. As the core structural unit of permethrin, benzfuryl alcohol has important economic and social value to realize its efficient synthesis. According to domestic and foreign literature reports, the synthesis of benzylfuryl alcohol is mainly carried out by first protecting 3-furanmethanol by hydroxyl group; 3-furanmethanol; then it is synthesized through six steps of benzyl chloride protection, phenyl lithium substitution and hydrog...

Claims

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Application Information

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IPC IPC(8): C07D307/58
CPCC07D307/58Y02P20/55
Inventor 倪春节袁晨秦淑雅王星孙雨心潘诗玉
Owner YANCHENG TEACHERS UNIV
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