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Synthesis method of beta-cyano ketone compound

A synthesis method and compound technology, which are applied in electrolysis process, electrolysis components, electrolysis organic production, etc., can solve the problems of unstable raw material aldehyde, narrow substrate range, high cost, short time required for reaction, short synthesis steps, low cost effect

Inactive Publication Date: 2022-01-21
CHANGZHOU INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantages of this method for preparing β-cyanoketones include: the use of a toxic trimethylsilyl cyano group, the instability of the raw material aldehyde, the use of metals and oxidants, the narrow range of substrates, and the It takes a long time and high cost

Method used

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  • Synthesis method of beta-cyano ketone compound
  • Synthesis method of beta-cyano ketone compound
  • Synthesis method of beta-cyano ketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] A synthetic method for β-cyanoketones, comprising the following steps:

[0041] (1) Add 0.45mmol of 4-methylbenzaldehyde formic acid and 0.6mmol of sodium hydroxide in a 10mL electrolytic cell without diaphragm, then add 4mL of acetonitrile to dissolve and stir for 10 minutes to obtain a solution;

[0042] (2) Continue to add 0.3mmol of 4-bromostyrene, 0.3mmol of cyanobenzodoxolone and 0.3mmol of lithium perchlorate in the above-mentioned solution and stir to obtain a mixed solution;

[0043] (3) With the platinum sheet (10×10×0.1mm) as the positive pole, with the graphite rod (I=0.6mm) as the negative pole, a constant current of 5mA was used to carry out the electrochemical reaction for 8 hours;

[0044] (4) After the reaction, collect the reaction solution and add it to a separatory funnel, add 20mL of water and stir, then extract the aqueous phase with ethyl acetate, dry the organic phase with anhydrous sodium sulfate, and purify and separate by column chromatography...

Embodiment 2

[0049] A synthetic method for β-cyanoketones, comprising the following steps:

[0050] (1) Add 0.45mmol of benzaldehyde formic acid and 0.6mmol of sodium hydroxide in a 10mL electrolytic cell without a diaphragm, then add 4mL of acetonitrile to dissolve and stir for 10 minutes to obtain a solution;

[0051] (2) Continue to add 0.3mmol of 4-methyl styrene formate, 0.3mmol of cyanobenzodoxolone and 0.3mmol of lithium perchlorate in the above-mentioned solution and stir evenly to obtain a mixed solution;

[0052] (3) With the platinum sheet (10×10×0.1mm) as the positive pole, with the graphite rod (I=0.6mm) as the negative pole, a constant current of 5mA was used to carry out the electrochemical reaction for 8 hours;

[0053] (4) After the reaction, collect the reaction solution and add it to a separatory funnel, add 20mL of water and stir, then extract the aqueous phase with ethyl acetate, dry the organic phase with anhydrous sodium sulfate, and purify and separate by column chr...

Embodiment 3

[0057] A synthetic method for β-cyanoketones, comprising the following steps:

[0058] (1) Add 0.45mmol of benzaldehyde formic acid and 0.6mmol of sodium hydroxide in a 10mL electrolytic cell without a diaphragm, then add 4mL of acetonitrile to dissolve and stir for 10 minutes to obtain a solution;

[0059] (2) Continue to add 0.3mmol of 3-methylstyrene, 0.3mmol of cyanobenzodoxolone and 0.3mmol of lithium perchlorate in the above-mentioned solution and stir to obtain a mixed solution;

[0060] (3) With the platinum sheet (10×10×0.1mm) as the positive pole, with the graphite rod (I=0.6mm) as the negative pole, a constant current of 5mA was used to carry out the electrochemical reaction for 8 hours;

[0061] (4) After the reaction, collect the reaction solution and add it to a separatory funnel, add 20mL of water and stir, then extract the aqueous phase with ethyl acetate, dry the organic phase with anhydrous sodium sulfate, and purify and separate by column chromatography to o...

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Abstract

The invention discloses a synthesis method of a beta-cyano ketone compound, which comprises the following steps: (1) adding alpha-ketonic acid and sodium hydroxide into a diaphragm-free electrolytic tank, and then adding acetonitrile for dissolving and stirring to obtain a dissolved solution; (2) continuously adding olefin or a derivative thereof, cyanobenziodoxolone and electrolyte into the dissolving solution, and uniformly conducting stirring to obtain a mixed solution; (3) taking a platinum sheet as a positive electrode and a graphite electrode as a negative electrode, conducting electrifying and carrying out electrochemical reaction; and (4) after the reaction, collecting reaction liquid, adding water, conducting stirring, extracting, drying and purifying to obtain the beta-cyano ketone compound. According to the synthesis method of the beta-cyano ketone compound, the beta-cyano ketone compound is prepared by taking alpha-ketonic acid, olefin or a derivative thereof and cyano benzoxone as raw materials and acetonitrile as a solvent through an electrochemical method. The synthesis method provided by the invention has the advantages of high product yield, low toxicity of used raw materials, mild reaction conditions, simple synthesis steps and low cost.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing β-cyanoketone compounds. Background technique [0002] The structure of β-cyanoketone compound is shown in (III) below, where R in formula III 1 , R 2 For different functional groups, aryl or alkyl. In the field of organic synthesis, β-cyanoketones are very common cyano- and carbonyl-containing compounds, which are widely used in biologically active natural products, drugs, and functional materials. In addition, the cyano group is a very important and common functional group. In chemical reactions, the cyano group can be converted into various functional groups such as carboxylic acid, amide, aldehyde, ketone and amino acid through a series of transformations, so as to realize the preparation of different compounds . [0003] [0004] At present, the main method of preparing β-cyanoketones is to synthesize α,β-unsaturated ketones throug...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/09C25B3/07
CPCC25B3/09C25B3/07B01D15/08C25B3/11C25B3/29C25B11/043C25B11/042C25B15/085
Inventor 陈小卉孔宪强陈依漪
Owner CHANGZHOU INST OF TECH