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Method for synthesizing 2-formyl-1-cyclopropane ethyl formate

A technology of ethyl cyclopropane formate and formyl, which is applied in the field of chemical pharmacy, can solve the problems of ethyl diazoacetate being explosive, immature synthesis method, and difficult to apply to ordinary industrial production, etc., and achieve high purity and low experimental cost. Effect

Pending Publication Date: 2022-01-14
西安都创医药科技有限公司
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  • Application Information

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Problems solved by technology

[0002] Ethyl 2-formyl-1-cyclopropanecarboxylate is commonly used as a drug synthesis intermediate segment, and the existing synthetic method is still immature; the structural formula of ethyl 2-formyl-1-cyclopropanecarboxylate is:
[0005] In view of the related technologies mentioned above, the inventor believes that the reaction raw material ethyl diazoacetate is explosive, and the reaction temperature condition is at -78°C, so there is a problem that this experimental scheme is difficult to be applied in general industrial production

Method used

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  • Method for synthesizing 2-formyl-1-cyclopropane ethyl formate
  • Method for synthesizing 2-formyl-1-cyclopropane ethyl formate
  • Method for synthesizing 2-formyl-1-cyclopropane ethyl formate

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Embodiment 1

[0044] A method for synthesizing ethyl 2-formyl-1-cyclopropanecarboxylate, comprising the steps:

[0045] Step Ⅰ: Synthesis of the first product ((ethoxycarbonylmethyl) dimethylsulfonium bromide)

[0046] Add 234.0g ethyl bromoacetate, 1.0L acetone, and 130.0g dimethyl sulfide to a 2L reactor, stir and react for 20 hours under nitrogen protection and room temperature to obtain reaction solution 1; after the reaction, filter, filter The cake was washed twice with 150.0 mL of acetone, the filtrate was drained, and dried under reduced pressure to obtain the first product (the molar ratio of ethyl bromoacetate to dimethyl sulfide was 1:1.49, and the molar ratio of ethyl bromoacetate to acetone for 1kg: 4.27L);

[0047] Step Ⅱ: Synthesis of the second product (ethyl 2-formyl-1-cyclopropanecarboxylate)

[0048] IIa. Add 100.0g (ethoxycarbonylmethyl) dimethylsulfonium bromide and 500.0mL chloroform to a 2L reactor, stir, and then add 505.0g saturated potassium carbonate dropwise un...

Embodiment 2

[0053] The difference with Example 1 is:

[0054] Step Ⅰ: Synthesis of the first product ((ethoxycarbonylmethyl) dimethylsulfonium bromide)

[0055] Add 234.0g ethyl bromoacetate, 1.4L acetone and 434.9g dimethyl sulfide to a 2L reactor, stir and react under nitrogen protection and room temperature for 20 hours to obtain reaction solution 1 (ethyl bromoacetate and dimethyl The molar ratio of sulfur is 1:5, the dosage ratio of ethyl bromoacetate and acetone is 1kg:6L);

[0056] Step Ⅱ: Synthesis of the second product (ethyl 2-formyl-1-cyclopropanecarboxylate)

[0057] IIa. Add 100.0g (ethoxycarbonylmethyl) dimethylsulfonium bromide and 120.5mL chloroform to the 2L reactor;

[0058] IIb. Add the intermediate to another 2L reaction flask, protect it with nitrogen, stir, and when the temperature is lowered to 0°C, add 120.0g of acrolein (the molar ratio of acrolein to the intermediate is 5:1).

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Abstract

The invention relates to the field of chemical pharmacy, and particularly discloses a method for synthesizing 2-formyl-1-cyclopropane ethyl formate. The preparation method comprises the following steps: I, mixing ethyl bromoacetate, dimethyl sulfide and an organic solvent 1 to obtain a first product; and II, mixing the first product with an organic solvent 2, stirring, cooling to -10-0 DEG C, adding an alkaline aqueous solution, reacting to obtain an intermediate, cooling the intermediate to -10-0 DEG C, and mixing the intermediate with acrolein to obtain a second product. The synthesis method has the advantages of being high in safety and suitable for common industrial production.

Description

technical field [0001] The application relates to the field of chemical pharmacy, more specifically, it relates to a method for synthesizing ethyl 2-formyl-1-cyclopropanecarboxylate. Background technique [0002] Ethyl 2-formyl-1-cyclopropanecarboxylate is commonly used as a drug synthesis intermediate segment, and the existing synthetic method is still immature; the structural formula of ethyl 2-formyl-1-cyclopropanecarboxylate is: . [0003] In the related art, in the method for preparing ethyl 2-formyl-1-cyclopropanecarboxylate, the raw materials used are propenyl alcohol and ethyl diazoacetate, the solvent used is methylene chloride, ether or pentane, and the catalyst is HBF 4 ·OEt 2 , and the reaction conditions were -78°C. The synthesis steps are: acrolein and HBF 4 ·OEt 2 Add CH at 78°C 2 Cl 2 , and added dropwise with CH 2 Cl 2 dilute ethyl diazoacetate, and then the reaction mixture was stirred at -78°C for 24 hours to obtain ethyl 2-formyl-1-cyclopropanec...

Claims

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Application Information

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IPC IPC(8): C07C67/343C07C69/716C07C381/12C07C381/00
CPCC07C67/343C07C381/12C07C381/00C07C2601/02C07C69/716
Inventor 胡海军王龙得单玉庆
Owner 西安都创医药科技有限公司
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