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Synthetic process of 1, 1-cyclopropane dicarboxylic acid dimethyl ester

A technology of dimethyl diformate and dimethyl malonate, which is applied in the field of synthesis of pharmaceutical raw material intermediates, can solve the problems of high boiling point and difficult recovery of polyethylene glycol dimethyl ether, and saves reaction time and is easy to operate. , the effect of cheap and easy-to-obtain raw materials

Inactive Publication Date: 2014-06-18
ZHANG JIA GANG VINSCE BIO PHARM
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  • Summary
  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this method, polyethylene glycol dimethyl ether has a high boiling point and is not easy to recover

Method used

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  • Synthetic process of 1, 1-cyclopropane dicarboxylic acid dimethyl ester

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Effect test

Embodiment 1

[0019] 17.8mL (0.21 mol) dimethyl malonate, 57.2mL (0.66 mol) dibromoethane, 33.1g (0.24 mol) potassium carbonate, 0.26g (0.8 mmol) tetrabutylammonium bromide, 50mL N, N-dimethylformamide joins in the reaction bottle of band condenser and water trap, 120 o C reacted for 3h. After the reaction, dibromoethane and N,N-dimethylformamide were recovered by distillation under reduced pressure, dichloromethane was added to the residue, stirred and filtered, and the filtrate was concentrated to obtain 28.2 g of dimethyl 1,1-cyclopropanedicarboxylate , yield 85%.

Embodiment 2

[0021] 17.8mL (0.21 mol) dimethyl malonate, 54.6mL (0.63 mol) dibromoethane, 29.0g (0.21 mol) potassium carbonate, 0.26g (0.8 mmol) tetrabutylammonium bromide, 50mL N, N-dimethylformamide joins in the reaction bottle of band condenser and water trap, 110 o C reacted for 3h. After the reaction, dibromoethane and N,N-dimethylformamide were recovered by distillation under reduced pressure, dichloromethane was added to the residue, stirred and filtered, and the filtrate was concentrated to obtain 24.9 g of dimethyl 1,1-cyclopropanedicarboxylate , yield 75%.

Embodiment 3

[0023] 17.8mL (0.21 mol) dimethyl malonate, 63.7mL (0.74 mol) dibromoethane, 33.1g (0.24 mol) potassium carbonate, 0.34g (1.1 mmol) tetrabutylammonium bromide, 50mL N, N-dimethylformamide joins in the reaction bottle of band condenser and water trap, 130 o C reacted for 3h. After the reaction, dibromoethane and N,N-dimethylformamide were recovered by distillation under reduced pressure, dichloromethane was added to the residue, stirred and filtered, and the filtrate was concentrated to obtain 28.9 g of dimethyl 1,1-cyclopropanedicarboxylate , yield 87%.

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Abstract

The invention relates to a synthetic process of 1, 1-cyclopropane dicarboxylic acid dimethyl ester, and belongs to the technical field of pharmaceutical raw material intermediate synthesis. The synthetic process is characterized in that dimethyl malonate reacts with dibromoethane under the effect of a phase transfer catalyst under an alkaline condition, and thus 1, 1-cyclopropane dicarboxylic acid dimethyl ester is obtained. The preparation method has the advantages that the raw materials are easy to obtain, conditions are mild, technological operation and controllability are strong, the cost is low, and the yield is high.

Description

technical field [0001] The invention belongs to the technical field of synthesis of pharmaceutical raw material intermediates, and in particular relates to a synthesis method of dimethyl 1,1-cyclopropanedicarboxylate. Background technique [0002] The chemical formula of dimethyl 1,1-cyclopropanedicarboxylate is: C 7 h 10 o 4 , is an important intermediate raw material for the synthesis of chemical drugs. [0003] The literature (Tetrahedron Letters, 46(4), 635-638; 2005) uses dimethyl malonate as raw material, potassium carbonate as base, and imidazole-type ionic liquid as phase transfer catalyst, and dibromoethane has a high yield at room temperature. Yield dimethyl 1,1-cyclopropanedicarboxylate. The synthesis process of imidazole-type ionic liquids in this method is relatively cumbersome, which is only suitable for laboratory research and is not easy for mass production. Document (Ger. Offen., 10003986, 2001) uses dimethyl malonate as raw material, potassium carbonat...

Claims

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Application Information

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IPC IPC(8): C07C69/74C07C67/343
CPCC07C67/343C07C2601/02C07C69/74
Inventor 赵金召张梅彭学东杨莲
Owner ZHANG JIA GANG VINSCE BIO PHARM
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