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

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Problems solved by technology

However, these methods must use paraformaldehyde raw materials and special trifluoroacetic acid secondary amine salt catalysts, which are

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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