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Synthesis method of 2-methylthio maleic acid diester compound

A technique for the synthesis of methylthiomaleic acid diester compounds, which is applied in the field of synthesis of 2-methylthiomaleic acid diester compounds, can solve problems such as the inability to realize the construction of thiomaleic acid diester compounds, and achieve functional group compatibility Good, simple reaction steps, high yield

Inactive Publication Date: 2021-07-06
HUNAN UNIV OF SCI & ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the reaction of sulfur-containing reagents and butynedioic acid diesters in the above method has introduced carbon-sulfur bonds, due to stereoselective reasons, the construction of thiomaleic acid diesters cannot be realized.

Method used

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  • Synthesis method of 2-methylthio maleic acid diester compound
  • Synthesis method of 2-methylthio maleic acid diester compound
  • Synthesis method of 2-methylthio maleic acid diester compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～3

[0040] The following examples 1 to 3 are all reacted under optimal reaction conditions, and the specific reaction equation is as follows, mainly to investigate the yield situation of different substrates reacting under optimal conditions:

[0041]

[0042] The specific operation steps are: in an 8mL reaction flask, add butynedioic acid diester (1.0mmol), diisopropylethylamine (0.1mmol), iodine element (0.5mmol), dimethyl sulfoxide (2.0mL ). The resulting mixture was stirred and reacted at 105°C, and the reaction progress was monitored by thin-layer chromatography, and the reaction time was 8 hours. After the reaction, 10ml of water was added to the reaction mixture, extracted with ethyl acetate (5ml×2), the organic phases were combined and washed with saturated brine, dried, concentrated in vacuo and purified by chromatographic column chromatography to obtain the target compound .

Embodiment 1

[0044] Compound 1: yield 93%, diethyl 2-(methylthio)maleate;

[0045]

[0046] 1 H NMR (400MHz, CDCl 3 )δ5.63(s,1H),4.35(q,J=7.2Hz,2H),4.17(q,J=7.2Hz,2H),2.37(s,3H),1.36(t,J=7.2Hz, 3H), 1.27(t, J=7.2Hz, 3H);

[0047] 13 C NMR (100MHz, CDCl 3 )δ165.5, 163.5, 151.1, 112.1, 62.4, 60.7, 14.6, 14.1, 13.9.

Embodiment 2

[0049] Compound 2: 92% yield, dimethyl 2-(methylthio)maleate;

[0050]

[0051] 1 H NMR (400MHz, CDCl 3 )δ5.65(s,1H),3.90(s,3H),3.72(s,3H),2.37(s,3H);

[0052] 13 C NMR (100MHz, CDCl 3 )δ166.0, 164.1, 151.4, 111.7, 53.2, 51.8, 14.6.

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Abstract

The invention discloses a synthesis method of a 2-methylthio maleic acid diester compound. According to the method, butynediacid diester, iodine elementary substance and dimethyl sulfoxide are subjected to a multi-component one-pot reaction, and the 2-methylthio maleic acid diester compound is obtained. According to the method, a metal catalyst does not need to be additionally added, the 2-methylthio maleic acid diester compound is obtained in a high-selectivity and high-yield mode under the mild condition, the reaction atomic efficiency is high, the cost is low, the method is environmentally friendly, separation and purification are simple, and large-scale production is facilitated.

Description

technical field [0001] The present invention relates to a kind of synthetic method of 2-methylthiomaleic acid diester compound. In particular, it relates to a method for synthesizing 2-methylthiomaleic acid diester compound through multi-component one-pot reaction of butyndioic acid diester, iodine simple substance and dimethyl sulfoxide under the condition of no external metal catalyst. Technical field of organic intermediate synthesis. Background technique [0002] As an important class of functionalized alkenes, 2-methylthiomaleic acid diester compounds not only have biologically active groups and modifiable groups, which play an important role in the field of drug research and development, but also can be used as important compounds in synthetic chemistry. The intermediates of various functional groups are transformed. At present, there are relatively few studies on the reaction of butynedioic acid diesters to construct carbon-sulfur bonds in one step. In 2011, Sarrafi...

Claims

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Application Information

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IPC IPC(8): C07C319/14C07C323/54
CPCC07C319/14
Inventor 芦玲慧吴超周强王毅
Owner HUNAN UNIV OF SCI & ENG
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