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Method for preparing alpha-carbonyl epoxy compound

A compound, phenyl technology, applied in the field of preparing alpha carbonyl epoxy compounds, can solve problems such as limited application, and achieve the effects of simple operation, wide adaptability and high yield

Inactive Publication Date: 2013-05-22
RENMIN UNIVERSITY OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These synthetic methods need to use α, β-unsaturated aldehydes or ketones as reaction substrates, which have great limitations in practical application.
In addition, the synthesis of α, β-unsaturated aldehydes or ketones also has certain limitations, which limits the application of these existing methods, especially the synthesis of multi-substituted epoxy compounds

Method used

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  • Method for preparing alpha-carbonyl epoxy compound
  • Method for preparing alpha-carbonyl epoxy compound
  • Method for preparing alpha-carbonyl epoxy compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0072] Embodiment 2: method one prepares 3,3-diphenyl-2,3-epoxy-1-propiophenone (R 1 is phenol group, R 2 is phenol group, R 3 for phenol group)

[0073]

[0074] 1) Under the protection of high-purity nitrogen, add 0.0125mmol FeCl to a 20mL Schlenk reaction tube 2 , compound 1 shown in 0.5mmol formula II, 1-stilbene, compound benzaldehyde shown in 2.5mmol formula III, compound tert-butanol peroxide (TBHP) shown in 3ml solvent acetonitrile and 1.5mmol formula IV, the above-mentioned mixed solution Stir the reaction at 85° C. under reflux for 1 hour to complete the reaction, and obtain a red reaction mixture, then add a little silica gel, then rotate the mixture to form a powder, and then separate it with an acidic silica gel column (silica gel: 200-300 mesh, The eluent is a mixed solution of diethyl ether and petroleum ether with a volume ratio of 1:100), and the yield is 93% of the intermediate product;

[0075] 2) Under the protection of high-purity nitrogen, dissolve...

Embodiment 3

[0083] Embodiment 3: Method one prepares compound (anti)-3-(4-pyridyl)-2,3-epoxy-1-propiophenone (R 1 for hydrogen, R 2 is pyridyl, R 3 for phenol group)

[0084]

[0085] 1) Under the protection of high-purity nitrogen, add 0.0125mmol FeCl to a 20mL Schlenk reaction tube 2 , compound 4-vinylpyridine shown in 0.5mmol formula II, compound benzaldehyde shown in 2.5mmol formula III, compound tert-butanol peroxide (TBHP) shown in 3ml solvent acetonitrile and 1.5mmol formula IV, above-mentioned mixed solution is at 85 Stir the reaction under reflux for 1 hour to complete the reaction, and obtain a red reaction mixture, then add a little silica gel, then rotate the mixture to form a powder, and then use an acidic silica gel column to separate (silica gel: 200-300 mesh, eluting The agent is a mixed solution of ethyl acetate and petroleum ether with a volume ratio of 1:20 plus 5 drops of ammonia water), and the yield is 39% of the intermediate product;

[0086]2) Under the prot...

Embodiment 4

[0094] Embodiment 4: Method one prepares compound 3-phenyl-2,3-epoxy-1-butyrophenone (R 1 is methyl, R 2 is phenol group, R 3 for phenol group)

[0095]

[0096] 1) Under the protection of high-purity nitrogen, add 0.0125mmol FeCl to a 20mL Schlenk reaction tube 2 , compound 1-methylstyrene shown in 0.5mmol formula II, compound benzaldehyde shown in 2.5mmol formula III, compound tert-butanol peroxide (TBHP) shown in 3ml solvent acetonitrile and 1.5mmol formula IV, above-mentioned mixed solution is in Stir the reaction under reflux at 85°C for 2 hours to complete the reaction, and obtain a red reaction mixture, then add a little silica gel, then rotate the mixture to form a powder, and then use an acidic silica gel column to separate (silica gel: 200-300 mesh, wash The deagent is a mixed solution of diethyl ether and sherwood oil with a volume ratio of 1:100), and the yield is 74% of the intermediate product;

[0097] 2) Under the protection of high-purity nitrogen, diss...

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Abstract

The invention discloses a method for preparing an alpha-carbonyl epoxy compound, which prepares the alpha-carbonyl epoxy compound by reacting a compound of a formula (I), a compound of a formula (II), a compound of a formula (III) and a compound of a formula (IV) in an organic solvent and reacting the product of the reaction with alkali. In the method, because a very cheap and environment-friendly metal is used as a catalyst, the reaction substrate has high adaptability, the operation is simple and convenient, the yield is high, and the product is easy to separate; and the method is suitable to prepare multisubstituted alpha-carbonyl epoxy compounds with different substituent groups and has a bright application prospect.

Description

technical field [0001] The present invention relates to a method for preparing alpha carbonyl epoxy compounds. Background technique [0002] Epoxy compounds are a class of compounds widely used in the fields of organic chemistry and polymer chemistry. They are important intermediates in organic synthetic chemistry and are widely used in fine chemicals, medical and pesticide raw materials and resin raw materials, as well as electronic information materials and optical materials. Such as synthesis and industrial production. A series of compounds containing hydroxyl groups, aldehyde groups, etc. can be synthesized through epoxy compounds. At the same time, epoxides are also high-value intermediates for the synthesis of chiral target products, and a series of important chiral compounds can be synthesized through epoxides. [0003] The main methods of synthesizing epoxy compounds are: (1) Olefin epoxidation. Obtained by the reaction of olefins with peroxides (reagents that don...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D301/19C07D303/32C07D405/04C07D407/06C07D409/06C07D303/48B01J23/745
Inventor 李志平刘为萍
Owner RENMIN UNIVERSITY OF CHINA