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A kind of preparation method of benzofuran compound

A compound and methyl technology, applied in the field of preparation of benzofuran compounds, can solve the problems of harsh conditions, complex preparation methods, poor environmental protection and the like, and achieve the effects of low cost, simple and convenient operation, and wide application range

Active Publication Date: 2018-09-14
ZHEJIANG SHENGXIAO CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to provide a preparation method of benzofuran compounds, which solves the problems of complex preparation methods, harsh conditions and poor environmental protection of existing benzofuran compounds

Method used

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  • A kind of preparation method of benzofuran compound
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  • A kind of preparation method of benzofuran compound

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preparation example Construction

[0032] According to one aspect of the present invention, there is provided a method for preparing benzofuran compounds, the method comprising: under a nitrogen atmosphere, in the presence of an organic solvent, using persulfate as an oxidant, trimethylsilyl group-protected P-methoxyphenol compounds and aromatic olefin compounds are stirred and reacted under heating conditions, and after reacting for a certain period of time, benzofuran compounds are obtained through separation and purification.

[0033] In the present invention, examples of the "halogen" include F, Cl, Br, I, etc., preferably F, Cl, Br.

Embodiment 1

[0039] Add 40mg 4-methoxyphenoxytrimethylsilane, 145mg sodium persulfate and 85mg styrene to a 10mL round bottom flask, seal the flask and replace nitrogen 3 times, add 2ml of acetonitrile to the reaction flask with a needle, at 50 Reaction at ℃ for 72h. After the reaction, the reaction solution was filtered, concentrated and spin-dried, and then the mixed solution of petroleum ether: ethyl acetate with a volume ratio of 30:1 was used as an eluent to perform purification and separation by silica gel column chromatography to obtain 2-phenyl -5-methoxy-2,3-dihydrobenzofuran, whose structural formula is:

[0040]

[0041] The obtained 2-phenyl-5-methoxy-2,3-dihydrobenzofuran was a colorless liquid with a yield of 72%, and its NMR data was: 1 H NMR (400MHz, CDCl 3 )δ7.42–7.30(m,5H),6.83–6.73(m,2H),6.70(dd,J=8.6,2.6Hz,1H),5.74(t,J=8.8Hz,1H),3.77(s , 3H), 3.60 (dd, J=15.7, 9.3Hz, 1H), 3.20 (dd, J=15.7, 8.2Hz, 1H).

[0042] 13 C NMR (100MHz, CDCl 3 )δ 154.33, 153.81, 142.04,...

Embodiment 2

[0044] Add 40mg 4-methoxyphenoxytrimethylsilane, 97mg sodium persulfate and 85mg styrene to a 10mL round-bottomed flask, seal the flask and replace nitrogen 3 times, add 2ml acetonitrile to the reaction flask with a needle, at 50 Reaction at ℃ for 72h. After the reaction, the reaction solution was filtered, concentrated and spin-dried, and then the mixed solution of petroleum ether: ethyl acetate with a volume ratio of 30:1 was used as the eluent to perform purification and separation by silica gel column chromatography to obtain 2-phenyl -5-methoxy-2,3-dihydrobenzofuran, whose structural formula is:

[0045]

[0046] The obtained 2-phenyl-5-methoxy-2,3-dihydrobenzofuran was a colorless liquid with a yield of 29%, and its NMR data was: 1 H NMR (400MHz, CDCl 3 )δ7.42–7.30(m,5H),6.83–6.73(m,2H),6.70(dd,J=8.6,2.6Hz,1H),5.74(t,J=8.8Hz,1H),3.77(s , 3H), 3.60 (dd, J=15.7, 9.3Hz, 1H), 3.20 (dd, J=15.7, 8.2Hz, 1H).

[0047] 13 C NMR (100MHz, CDCl 3 )δ 154.33, 153.81, 142.04, ...

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Abstract

The invention provides a preparation method of a benzofuran compound. The method comprises the following steps of: in a nitrogen atmosphere and in the presence of persulfate and an organic solvent, enabling a p-methoxyphenol compound protected by a trimethylsilyl group to react with an aromatic olefin compound. The method provided by the invention has the advantages of simple start raw materials, no metal catalysis, mild reaction conditions and easiness in operation, is a green environment-friendly chemical technology and can be widely used for preparing benzofuran compounds; and the synthesis of a natural product corsifuran A can be finished in one step by the method.

Description

technical field [0001] The invention relates to a preparation method of benzofuran compounds. Background technique [0002] Benzofuran compounds are a class of important heterocyclic compounds with diverse structures, which widely exist in natural products and synthetic drugs, and have potential biological activities and pharmacological properties, such as anti-inflammatory, anti-cancer, anti-oxidation and other physiological functions. Among them, the 2,3-dihydrobenzofuran skeleton represents the core structure of many biologically and pharmacologically active compounds, such as compounds 1-4 shown below, so more and more people are working on benzofuran compounds synthesis research. [0003] [0004] At present, there are many reports on the preparation of dihydrobenzofuran compounds, but there are still many shortcomings, for example, the reaction starting materials are complicated, multi-step synthesis is required, the reaction conditions are harsh, and metal catalys...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/79C07D307/80C07D307/93
Inventor 夏吾炯赵亚婷郭小忠冯永胜杨双土洪国良章丽袁鹏程林巧
Owner ZHEJIANG SHENGXIAO CHEM
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