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Synthetic method of diazomethane compound

A synthesis method and diazomethane technology are applied in the preparation of organic compounds, organic chemistry methods, chemical instruments and methods, etc., which can solve problems such as environmental hazards and increased operation difficulty, and achieve low energy demand and simple post-processing process. , to avoid the effect of silica gel column chromatography separation

Inactive Publication Date: 2012-11-21
SHENZHEN Y GENE BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] This route needs to use nitrosyl chloride as a raw material, and nitrosyl chloride is a highly toxic gas, which makes the operation of the reaction more difficult and brings great harm to the environment

Method used

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  • Synthetic method of diazomethane compound
  • Synthetic method of diazomethane compound
  • Synthetic method of diazomethane compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The synthesis of embodiment 1 p-toluenesulfonyl acetate-3,3,5-trimethyl-2-cyclohexenol ester

[0041]

[0042] 3,3,5-trimethyl-2-cyclohexenol (6mmol) was dissolved in dichloromethane (10ml), and 4-dimethylaminopyridine (DMAP) (0.6mmol) was added to the reaction system, Further dicyclohexylcarbodiimide (DCC) (6.6 mmol) was dissolved in dichloromethane (6 ml) and added to the solution. After 5 minutes, p-toluenesulfonylacetic acid (6.6 mmol) was added to the reaction system, and the clear liquid immediately became turbid. Stir at room temperature for 12 hours. The solid in the flask was filtered off and the filtered solid was washed with EtOAc (20ml). The filtrate was washed with potassium bisulfate (1M, 20ml×3), saturated sodium bicarbonate (20ml×3), saturated brine (20ml×3), and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure and purified by silica gel column chromatography (ethyl acetate: petroleum ether) to obtain the...

Embodiment 2

[0043] The synthesis of embodiment 2 p-toluenesulfonyl acetate-2-cyclohexenol ester

[0044] 2-cyclohexenol was dissolved in dichloromethane, DMAP was added to the reaction system, DCC was dissolved in dichloromethane and then added to the solution. After 5 minutes, p-toluenesulfonylacetic acid was added to the reaction system, and the clear liquid immediately became turbid. Stir at room temperature for 12 hours. The solid in the flask was filtered off and the filtered solid was washed with EtOAc (20ml). The filtrate was washed with potassium bisulfate (1M, 20ml×3), saturated sodium bicarbonate (20ml×3), saturated brine (20ml×3), and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure and purified by silica gel column chromatography (ethyl acetate: petroleum ether) to obtain the obtained product.

Embodiment 3

[0045] The synthesis of embodiment 3 p-toluenesulfonyl acetate allyl alcohol ester

[0046] Allyl alcohol was dissolved in dichloromethane, DMAP was added to the reaction system, DCC was dissolved in dichloromethane and then added to the solution. After 5 minutes, p-toluenesulfonylacetic acid was added to the reaction system, and the clear liquid immediately became turbid. Stir at room temperature for 12 hours. The solid in the flask was filtered off and the filtered solid was washed with EtOAc (20ml). The filtrate was washed with potassium bisulfate (1M, 20ml×3), saturated sodium bicarbonate (20ml×3), saturated brine (20ml×3), and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure and purified by silica gel column chromatography (ethyl acetate: petroleum ether) to obtain the obtained product.

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Abstract

The invention provides a synthetic method of a diazomethane compound. Diazotized sulfonyl-3,5,5-trimethyl-2-cyclohexenyl acetate is decarboxylated under the action of neutral alumina to obtain the high-purity and high-yield diazomethane compound. The synthetic method is carried out without using nitrosyl chloride which has the characteristics of high toxicity and easy blasting as a reaction raw material is environmentally-friendly and safe. The reaction yield is good, all the reactions are carried out with the temperature in a range from 0 to room temperature, and requirements on energy are low. The posttreatment process of the final product is simple, so expensive silica gel column chromatography separation is avoided. The reactant alumina has the effects of impurity separation and product purification, so the high-purity sulfonyl diazomethane derivative can be obtained through simple reduced pressure pumping filtration and concentration.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing diazomethane compounds. Background technique [0002] Diazo compounds are widely used in organic synthesis. The unique carbene properties of these molecules enable them to participate in numerous organic chemical reactions, such as cyclopropanation, activation of carbon-hydrogen bonds, and Wolff rearrangement, etc. Diazo compounds with electron-withdrawing groups, such as diazomethanes substituted by sulfonyl groups, acyl groups and ester groups, are very important raw materials in the fields of organic chemical research, drug research and development, and fine chemical product development. Due to the limitation of the molecular structure of diazomethane itself, as well as the explosive nature of heat and impact, many processes that can be quickly realized through diazo compounds can only be detoured in other ways. [0003] Taking sulfonyl diazomethane...

Claims

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Application Information

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IPC IPC(8): C07B43/00C07C317/32C07C315/04
Inventor 赵劲陈鹏陈兴
Owner SHENZHEN Y GENE BIOTECH CO LTD
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