Method for synthesizing benzofuran derivatives in one pot process

A technology for benzofuran and derivatives, which is applied in the field of one-pot synthesis of benzofuran derivatives, can solve the problems of high price, inapplicability of halogen-containing benzofuran, and limited sources of raw materials, and achieve low cost and applicable Wide Range of Selective Effects

Inactive Publication Date: 2012-07-18
BEIJING NORMAL UNIVERSITY
View PDF2 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The most prominent advantage of the above method is that it is versatile, the reaction is simple, and it is a "one-pot" synthesis. However, the sources of raw materials for this method are not extensive. For example, the alkynes used often require multi-step reactions to obtain
In addition, this method also needs to

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for synthesizing benzofuran derivatives in one pot process
  • Method for synthesizing benzofuran derivatives in one pot process
  • Method for synthesizing benzofuran derivatives in one pot process

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0029] Example 1, Preparation of 2-(3,4-dimethoxyphenyl)benzofuran

[0030]

[0031] Salicylaldehyde (0.61g, 5mmol), 3,4-dimethoxybenzyltriphenylphosphonium chloride (2.5g, 5.5mmol), potassium hydroxide (0.34g, 6.0mmol) were added to 50mL of toluene in sequence , Stir the reaction at room temperature (25°C) until the salicylaldehyde disappears substantially or completely. Add powdered anhydrous potassium carbonate (3.5g, 25.0mmol) to the system, stir for half an hour, if stirring is difficult, add toluene or tetrahydrofuran, add iodine (6.4g, 25.0mmol), stir at room temperature (25℃) until the reaction complete. 80mL saturated sodium bicarbonate solution was added to the reaction mixture, and protective sodium bisulfite solution was added dropwise until the color of the reaction solution faded. The resulting mixture was extracted with ethyl acetate (3×80mL), the organic layer was dried over anhydrous sodium sulfate, and the solvent was recovered The obtained crude product was p...

Example Embodiment

[0033] Example 2, 2-(3-Methoxy-4-benzyloxyphenyl)-6-methoxybenzofuran

[0034]

[0035] 4-methoxysalicylic aldehyde (0.76g, 5mmol), 3-methoxy-4-benzyloxybenzyltriphenylphosphonium chloride (2.9g, 5.5mmol), potassium hydroxide (0.70g, 12.5 mmol) was sequentially added to a thoroughly dried mortar, ground vigorously at room temperature (25°C) for 30 minutes, and then intermittently ground for 2 to 3 hours. The resulting paste was transferred to a 250 mL three-necked reaction flask, and 20 mL of tetrahydrofuran (or After washing the residue with toluene, transfer it to a reaction flask, add tetrahydrofuran (or toluene) to 50 mL, and stir and react at room temperature (25° C.) for 2 to 3 hours. Add powdered anhydrous potassium carbonate (3.5g, 25.0mmol) to the system, stir for half an hour, if stirring is difficult, add toluene or tetrahydrofuran, add iodine (6.4g, 25.0mmol), stir at room temperature (25℃) until the reaction complete. 80mL saturated sodium bicarbonate solution was ...

Example Embodiment

[0041] Example 3. Methyl 4-(7-methoxy-2-benzofuranyl)benzoate

[0042]

[0043] 3-Methoxysalicylic aldehyde (0.76g, 5mmol), 4-formate methylbenzyltriphenylphosphonium chloride (2.5g, 5.5mmol), potassium hydroxide (0.6g, 6.0mmol) were added to In 50 mL of toluene, the reaction was stirred at room temperature (25° C.) until the 3-methoxy salicylaldehyde disappeared substantially or completely. Add glacial acetic acid (0.40g, 6mmol) dropwise to the system, add dichlorodicyanobenzoquinone (DDQ) (1.7g, 7.5mmol), and heat to reflux until the reaction is complete. 80 mL of saturated sodium bicarbonate solution was added to the reaction mixture, the resulting mixture was extracted with ethyl acetate (3×80 mL), the organic layer was dried over anhydrous sodium sulfate, the solvent was recovered, and the crude product obtained was purified by column chromatography to obtain the target product 4-(7 -Methoxy-2-benzofuryl) benzoic acid methyl ester, yield: 69%.

[0044] The prepared product w...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention relates to a method for synthesizing benzofuran derivatives in a one pot process, which includes the following steps: (1) adding quaternary phosphonium salt or phosphite ester salt and inorganic alkali or organic alkali in salicylaldehyde or salicylaldehyde derivatives, mixing and stirring materials in solvents or leading the materials to be in solid phase and to be grinded for reaction in solvent-free conditions so as to generate 2-styryl phenol derivatives, and (2) adding oxidants into the 2-styryl phenol derivatives obtained through the step (1) in normal position mode for oxidation and cyclization to obtain the benzofuran derivatives. The method has the advantages of being simple and smooth by operating in the one pot process, mild in conditions, easy to magnify, especially suitable for industrial production, wide in application range, high in yield and low in cost.

Description

Technical field [0001] The present invention relates to the preparation field of benzofuran derivatives. Specifically, the present invention relates to a one-pot method for synthesizing benzofuran derivatives. Background technique [0002] Benzofuran and its derivatives are an important class of benzoheterocyclic compounds, occupying a very important position in natural product chemistry and medicinal chemistry. For example, Cicerfuran (I) shows good antibacterial and antifungal effects [Stevenson P.C., Veitch N.C. Phytochemistry, 1998, 48, 995]. Another example is the compound Ailanthoidol (II) isolated and extracted from the traditional Chinese medicine Zanthoxylum ailanthoides, which has a wide range of biological activities such as anti-tumor, anti-viral, immunosuppressive, anti-oxidant, anti-fungal and anti-free radical activities [Kao CL, Chern J. W, J. Org. Chem., 2002, 67, 6772]. In addition, a large number of benzofuran derivatives, such as oleanol [Egonol(III)], Corsi...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07B41/04C07D307/80C07D307/79C07D409/04C07D407/04C07D493/04C07D307/92
Inventor 段新方廖连燕沈刚段晓峰张雪
Owner BEIJING NORMAL UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap