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Method for synthesizing 3-methylene benzofuran-1(3H)-one compound

A technology for ketone compounds and methylene benzene is applied in the field of synthesizing 3-methylene benzofuran-1-one compounds, which can solve the problems of producing toxic by-products, harsh reaction conditions, expensive ligands and the like, and achieves the The effect of high yield, low cost of raw materials, and simple experimental operation

Active Publication Date: 2021-06-22
EAST CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although these methods provide a variety of options for the preparation of 3-methyleneisobenzofuran-1(3H)-one compounds, the above-mentioned methods still have harsh reaction conditions, expensive catalysts, ligands, and toxic by-products. limitation

Method used

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  • Method for synthesizing 3-methylene benzofuran-1(3H)-one compound
  • Method for synthesizing 3-methylene benzofuran-1(3H)-one compound
  • Method for synthesizing 3-methylene benzofuran-1(3H)-one compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Add benzhydryl alcohol (0.2mmol), 2-acetylbenzoic acid (0.3mmol), H 3 PMo 12 o 40 (1.5mol%) and chlorobenzene (1ml). Then react at 80° C. for 3 hours. After the reaction was finished, the target product was obtained by separation by column chromatography with a yield of 93%. When the raw material addition ratio is 1:1.0, the yield is 76%. When the raw material addition ratio is 1:1.3, the yield is 87%.

[0031] The specific results of the structural characterization of the target product are as follows:

[0032]

[0033] NMR spectroscopy data: 1 H NMR (500MHz, CDCl 3 )δ7.88(d, J=7.7Hz,1H),7.67(dd,J=6.1,3.2Hz,2H),7.51(ddd,J=7.9,5.3,2.9Hz,1H),7.37–7.27(m ,8H),7.25-7.22(m,2H),6.10(d,J=10.6Hz,1H),5.59(d,J=10.5Hz,1H); 13 C NMR (126MHz, CDCl 3 ) δ 166.9, 145.3, 142.9, 139.4, 134.5, 129.9, 128.8, 128.3, 126.8, 125.5, 124.7, 120.2, 110.5, 46.9.

[0034] High-resolution mass spectrometry data: HRMS (ESI): m / z, calcd.for C 22 h 17 o 2 [M+H] + requires 313.1223, ...

Embodiment 2

[0037] Add benzhydryl alcohol (0.2mmol), 4-methyl-2-acetylbenzoic acid (0.3mmol), H 3 PMo 12 o 40(1.5mol%) and chlorobenzene (1ml). Then react at 80° C. for 3 hours. After the reaction was finished, the target product was obtained by separation by column chromatography with a yield of 87%. When the raw material addition ratio is 1:1.0, the yield is 77%. When the raw material addition ratio is 1:1.3, the yield is 81%.

[0038] The specific results of the structural characterization of the target product are as follows:

[0039]

[0040] NMR spectroscopy data: 1 H NMR (500MHz, CDCl 3 )δ7.67(s,1H),7.56(d,J=8.0Hz,1H),7.48(d,J=7.9Hz,1H),7.34–7.27(m,8H),7.25–7.22(m,2H ), 6.02(d, J=10.5Hz, 1H), 5.57(d, J=10.5Hz, 1H), 2.46(s, 3H); 13 C NMR (126MHz, CDCl 3 ) δ 167.1, 145.3, 143.0, 140.6, 137.1, 135.7, 128.7, 128.3, 126.7, 125.3, 124.9, 119.9, 109.6, 46.9, 21.6.

[0041] High-resolution mass spectrometry data: HRMS (ESI): m / z, calcd.for C 23 h 19 o 2 [M+H] + requires 3...

Embodiment 3

[0044] Add benzhydryl alcohol (0.2mmol), 4-chloro-2-acetylbenzoic acid (0.3mmol), H 3 PMo 12 o 40 (1.5mol%) and chlorobenzene (1ml). Then react at 80° C. for 3 hours. After the reaction was finished, the target product was obtained by separation by column chromatography with a yield of 81%. When the raw material addition ratio is 1:1.0, the yield is 72%. When the raw material addition ratio is 1:1.3, the yield is 77%.

[0045] The specific results of the structural characterization of the target product are as follows:

[0046]

[0047] NMR spectroscopy data: 1 H NMR (500MHz, CDCl 3 )δ7.85(s,1H),7.64–7.59(m,2H),7.34–7.30(m,4H),7.29–7.22(m,6H),6.10(d,J=10.6Hz,1H),5.56 (d,J=10.5Hz,1H); 13 C NMR (126MHz, CDCl 3 ) δ 165.5, 144.6, 142.6, 137.6, 136.2, 134.8, 128.8, 128.3, 126.9, 126.3, 125.3, 121.4, 111.4, 47.1.

[0048] High-resolution mass spectrometry data: HRMS (ESI): m / z, calcd.for C 22 h 16 o 2 Cl[M+H] + requires 347.0833, found 347.0839;

[0049] The above...

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Abstract

The invention discloses a method for synthesizing a 3-methylene benzofuran-1(3H)-one compound, and belongs to the technical field of organic synthesis. According to the method, a diphenyl carbinol compound and a 2-acyl benzoic acid compound are subjected to a dehydration coupling reaction under the action of a polyoxometalate (POMs) catalyst, and the 3-methylene benzofuran-1(3H)-one compound is synthesized. According to the method, the efficient and green catalyst is used, the dosage of the catalyst is small, the reaction condition is mild, and the only by-product is water. The method provides a simple, efficient, high-yield and environment-friendly green synthesis method for synthesizing the 3-methylene benzofuran-1(3H)-one compound.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing 3-methylenebenzofuran-1(3H)-one compounds. Background technique [0002] 3-Methyleneisobenzofuran-1(3H)-one compound is an important phthalide compound, which widely exists in natural products and synthetic products, and exhibits a wide range of biological activities. For example, the natural product (Z)-3-butenyl-5-hydroxyphthalide has anti-inflammatory activity; the main component of Chinese medicine Angelica sinensis (Z)-3-n-butenylphthalide has anti-diabetic and anti-coagulant effects; other Natural products containing this skeleton exhibit anti-allergic, bactericidal, anti-AIDS and other activities. In addition, 3-methyleneisobenzofuran-1(3H)-one compounds are also an important intermediate skeleton structure in organic synthesis, which can be transformed into other nitrogen heterocyclic compounds with important biological activities. In...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/88
CPCC07D307/88Y02P20/584
Inventor 杨国平刘玉峰李可
Owner EAST CHINA UNIV OF TECH
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