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Method for synthesizing alpha,beta-unsaturated aryl ketone compound from dimethyl sulfoxide and arylethanone

A technology of dimethyl sulfoxide and aryl ethyl ketone, which is applied to the synthesis of α from dimethyl sulfoxide and aryl ethyl ketone, can solve the problems of unfavorable large-scale production, low safety and environmental protection, and complicated operation, and meet the requirements of Industrial production requirements, low cost, and high reaction selectivity

Active Publication Date: 2018-03-06
YUANJIANG HUALONG CATALYST TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods must use paraformaldehyde raw materials and special trifluoroacetic acid secondary amine salt catalysts, which are low in safety and environmental protection, high in cost, and complicated in operation, which is not conducive to large-scale production.

Method used

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  • Method for synthesizing alpha,beta-unsaturated aryl ketone compound from dimethyl sulfoxide and arylethanone
  • Method for synthesizing alpha,beta-unsaturated aryl ketone compound from dimethyl sulfoxide and arylethanone
  • Method for synthesizing alpha,beta-unsaturated aryl ketone compound from dimethyl sulfoxide and arylethanone

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Aryl ethyl ketone raw material:

[0047] α,β-Unsaturated aryl ketones products:

[0048] The reaction time is 9h, the product is a colorless oil, and the yield is 85%.

[0049] 1 H NMR (400MHz, CDCl 3 ): δ7.95(d, J=7.7Hz, 2H), 7.58(t, J=7.3Hz, 1H), 7.48(t, J=7.5Hz, 2H), 7.16(dd, J=17.1, 10.6Hz ,1H),6.44(d,J=17.1Hz,1H),5.94(d,J=10.6Hz,1H).

[0050] 13 C NMR (101MHz, CDCl 3 ): δ191.1, 137.2, 133.0, 132.4, 130.2, 128.7, 128.6.

Embodiment 2

[0052] Aryl ethyl ketone raw material:

[0053]α,β-Unsaturated aryl ketones products:

[0054] The reaction time is 9h, the product is light yellow oil, and the yield is 74%.

[0055] 1 H NMR (400MHz, CDCl 3 ): δ7.97(d, J=8.6Hz, 2H), 7.18(dd, J=17.0, 10.5Hz, 1H), 6.96(d, J=8.6Hz, 2H), 6.42(d, J=17.0Hz ,1H),5.87(d,J=10.5Hz,1H),3.88(s,3H).

[0056] 13 C NMR (101MHz, CDCl 3 ): δ189.2, 163.5, 132.1, 131.0, 130.2, 129.3, 113.8, 55.5.

Embodiment 3

[0058] Aryl ethyl ketone raw material:

[0059] α,β-Unsaturated aryl ketones products:

[0060] The reaction time was 9h, and the product was light yellow oil with a yield of 77%.

[0061] 1 H NMR (400MHz, CDCl 3 ): δ7.95(d, J=8.6Hz, 2H), 7.17(dd, J=17.1, 10.5Hz, 1H), 6.94(d, J=8.6Hz, 2H), 6.42(d, J=17.0Hz ,1H),5.86(d,J=10.5Hz,1H),4.10(q,J=7.0Hz,2H),1.44(t,J=7.0Hz,3H).

[0062] 13 C NMR (101MHz, CDCl 3 ): δ189.2, 163.0, 132.1, 131.0, 130.0, 129.1, 114.2, 63.7, 14.6.

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Abstract

The invention discloses a method for synthesizing an alpha,beta-unsaturated aryl ketone compound from dimethyl sulfoxide and arylethanone. According to the method, dimethyl sulfoxide and arylethanoneare subjected to a one-pot reaction in the presence of carboxylate and persulfate so as to produce the alpha,beta-unsaturated aryl ketone compound. The method uses dimethyl sulfoxide as a methylenation reagent and employs a one-pot process for high-selectivity high-yield synthesis of the alpha,beta-unsaturated aryl ketone compound from arylethanone; and the method is simple to operate, low in cost, friendly to environment and beneficial for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing α,β-unsaturated aryl ketones from dimethyl sulfoxide and aryl ethyl ketone, in particular to a method using dimethyl sulfoxide as The invention relates to a methylation reagent, which performs the α-(C)-H methylation reaction of aryl ethyl ketone, and a method for directly reacting and synthesizing α, β-unsaturated aryl ketone compounds, belonging to the technical field of pharmaceutical intermediates and synthesis. Background technique [0002] The α-functionalization reaction of ketones is of great significance in organic synthesis and has become the focus of research for many years. Especially α,β-unsaturated ketone compounds, because they contain modifiable double bonds, are a very important class of organic intermediates in drug synthesis. At present, many different methods for preparing α,β-unsaturated ketones have been reported. For example, the literature (Eur.J.Org.Chem.2015, 3044–3047) discl...

Claims

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Application Information

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IPC IPC(8): C07C49/794C07C45/68C07C49/84C07C49/807C07C49/796C07C253/30C07C255/56
CPCC07C45/68C07C253/30C07C49/794C07C49/84C07C49/807C07C49/796C07C255/56
Inventor 郭灿城刘玉峰郭欣
Owner YUANJIANG HUALONG CATALYST TECH
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