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One-pot synthesis method of (Z)-type sulfonyl olefine acid ester compound

A technology of sulfonyl alkenoate and synthesis method, applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve the problems of low selectivity, narrow substrate range, low atom economy, etc. The effect of simplified process steps, mild reaction conditions and wide application value

Inactive Publication Date: 2016-08-31
HUNAN UNIV OF SCI & ENG +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, there are many defects in these two methods. For example, it takes two-step reactions to obtain the target product from the raw material to the product, and various additives, metal catalysts, etc. are required; Defects such as low sex and low selectivity

Method used

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  • One-pot synthesis method of (Z)-type sulfonyl olefine acid ester compound
  • One-pot synthesis method of (Z)-type sulfonyl olefine acid ester compound
  • One-pot synthesis method of (Z)-type sulfonyl olefine acid ester compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]In a clean and dry 10 ml round bottom flask, add 49 mg of sodium p-toluene sulfinate and 74 mg of ethyl propiolate in sequence, use 2 ml of water as the reaction solvent, and stir at 70°C for 10 minutes. After the reaction was completed, it was extracted by adding ethyl acetate, and the upper organic phase was directly spin-dried and dissolved with a small amount of petroleum ether and ethyl acetate (30:1 by volume), and separated by a silica gel column to obtain 58.4 mg of a colorless liquid. Yield 92%.

[0034] 1 H NMR (400MHz, CDCl 3 )δ7.81(d, J=8.1Hz, 2H), 7.27(d, J=8.0Hz, 2H), 6.50–6.31(m, 2H), 4.29(q, J=7.1Hz, 2H), 2.39( s,3H),1.31(t,J=7.1Hz,3H); 13 CNMR (100MHz, CDCl 3 )δ164.03, 145.20, 136.50, 135.41, 131.42, 129.97, 128.28, 62.15, 21.69, 13.96.

Embodiment 2

[0036] In a clean and dry 10 ml round bottom flask, add 53 mg of sodium p-methoxyphenyl sulfinate and 74 mg of ethyl propiolate in sequence, and use 2 ml of water as the reaction solvent, and stir for 5 minutes at 50°C . After the reaction was completed, it was extracted by adding ethyl acetate, and the upper organic phase was directly spin-dried and dissolved with a small amount of petroleum ether and ethyl acetate (30:1 by volume), and separated by a short silica gel column to obtain 66.2 mg of colorless Liquid, 96% yield.

[0037] 1 H NMR (400MHz, CDCl 3 )δ7.92(d, J=8.7Hz, 2H), 7.05(d, J=8.7Hz, 2H), 6.532–6.40(m, 2H), 4.36(q, J=7.1Hz, 2H), 3.87( s,3H),1.38(t,J=7.1Hz,3H); 13 C NMR (100MHz, CDCl 3 )δ164.15, 164.12, 135.67, 130.88, 130.59, 114.57, 62.12, 55.72, 14.03.

Embodiment 3

[0039] In a clean and dry 10 ml round bottom flask, add 65 mg of sodium p-bromophenylsulfinate and 74 mg of ethyl propiolate in sequence, and use 2 ml of water as the reaction solvent, and stir at 45°C for 15 minutes. After the reaction, it was extracted by adding ethyl acetate, and the upper organic phase was directly spin-dried and dissolved with a small amount of petroleum ether and ethyl acetate (volume ratio of 30:1), separated by a short silica gel column to obtain 73.4 mg of white solid , yield 92%.

[0040] 1 H NMR (400MHz, CDCl 3 )δ7.88(d, J=8.4Hz, 2H), 7.72(d, J=8.4Hz, 2H), 6.52(s, 2H), 4.36(q, J=7.1Hz, 2H), 1.38(t, J = 7.2Hz, 2H); 13 C NMR (100MHz, CDCl 3 )δ163.77, 138.50, 135.01, 132.66, 132.55, 129.83, 129.54, 62.30, 13.98.

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Abstract

The invention discloses a one-pot synthesis method of a (Z)-type sulfonyl olefine acid ester compound. According to the method, the sulfonyl olefine acid ester compound is obtained by one-pot reaction of a sulfinic acid sodium and an acetylenic acid ester compound in the presence of water. The (Z)-type sulfonyl olefine acid ester compound is synthesized by one-pot reaction under mild conditions with the method, the method is simple to operate, environment friendly, free of additives and the like, and industrial production is facilitated.

Description

technical field [0001] The invention relates to a one-pot synthesis method of a (Z) formula sulfonylenoate compound, belonging to the field of organic synthesis. Background technique [0002] The carbon-carbon double bond is one of the most variable functional groups in the field of organic chemistry. Many reactions can synthesize carbon-carbon double bonds (Chem.Commun.2006,3646–3647; Synlett 2006,11,1783–1785). Among these reactions, The formation of monosubstituted coupled alkenes is an important reaction because these alkenes are very important intermediates and building blocks in natural products and optical materials (Adv. Mater. 2003, 15, 1176–1180; Polym. Chem. 2003 , 41, 674–683). In the past few decades, due to the special influence of sulfonyl functional groups on molecular structure stability, molecular activity and biological activity, organic chemists have tried to introduce them into organic molecules (Sulfones in Organic Synthesis; PergamonPress: Oxford, 19...

Claims

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Application Information

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IPC IPC(8): C07C315/00C07C317/44
CPCC07C315/00C07C317/44
Inventor 吴超曹忠何福林尹国兴杨盼盼
Owner HUNAN UNIV OF SCI & ENG
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