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Method for synthesizing 7-methoxyl-1-benzofuran-4-formaldehyde

A technology of benzofuran and methoxybenzene, applied in the field of medicine, can solve the problems of high price and low yield, and achieve the effects of low price, high safety and good controllability

Inactive Publication Date: 2017-04-26
天津羲泽润科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the problems of high price and low yield in the prior art, the invention provides a method for synthesizing 7-methoxy-1-benzofuran-4-carbaldehyde, which has high yield and low cost , simple operation, good safety, friendly to the environment, and suitable for industrial production

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  • Method for synthesizing 7-methoxyl-1-benzofuran-4-formaldehyde
  • Method for synthesizing 7-methoxyl-1-benzofuran-4-formaldehyde
  • Method for synthesizing 7-methoxyl-1-benzofuran-4-formaldehyde

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Embodiment 1

[0021] S1: Add 273.8g (1.8mol, 1.0eq) of o-vanillin and 197.4g (2.9mol, 1.6eq) of imidazole in a 5L four-neck flask with a mechanical stirrer and a thermometer, dissolved in 1.5L of DMF solution, and stir The system was allowed to clear for 1 hour. Then the temperature was lowered to between 0°C and 5°C, and 416g (2.2mol, 1.2eq) of triisopropyl silicon chloride was added dropwise under the protection of nitrogen, and the drop was completed within 30 minutes, and the reaction was continued for 1h to complete the reaction. Add 2L of ethyl acetate and 1L of water to the reaction system, separate the layers, wash the organic phase with 5% dilute hydrochloric acid and saline, dry over anhydrous sodium sulfate, filter, and concentrate the filtrate under reduced pressure to obtain 540g of 3-methoxy-2 - Triisopropylsiloxybenzaldehyde, yield 97.5%, purity 98% (HPLC).

[0022] S2: Add 308.5g (1.0mol, 1.0eq) 3-methoxy-2-triisopropylsilyloxybenzaldehyde, 276g (2.0mol, 2.0 eq) potassium ...

Embodiment 2

[0028] S1: Add 273.8g (1.8mol, 1.0eq) of o-vanillin and 306.3g (4.5mol, 2.5eq) of imidazole in a 5L four-neck flask with a mechanical stirrer and a thermometer, dissolved in 1.5L of DMF solution, and stir The system was allowed to clear for 1 hour. Then the temperature was lowered to between 0°C and 5°C, and 416g (2.2mol, 1.2eq) of triisopropyl silicon chloride was added dropwise under the protection of nitrogen, and the drop was completed within 30 minutes, and the reaction was continued for 1h to complete the reaction. Add 2L of ethyl acetate and 1L of water to the reaction system, separate the layers, wash the organic phase with 5% dilute hydrochloric acid and saline, dry over anhydrous sodium sulfate, filter, and concentrate the filtrate under reduced pressure to obtain 536g of 3-methoxy-2 - Triisopropylsilyloxybenzaldehyde, yield 96.8%, purity 98% (HPLC).

[0029] S2: Add 308.5g (1.0mol, 1.0eq) 3-methoxy-2-triisopropylsilyloxybenzaldehyde, 207g (1.5mol, 1.5eq) potassium...

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Abstract

The invention provides a new method for preparing 7-methoxyl-1-benzofuran-4-formaldehyde. The method comprises the steps of protecting a phenolic hydroxyl group of methoxysalicylaldehyde being a natural product and serving as a raw material with triisopropyl silicon chloride under the alkaline condition; then reacting an aldehyde group with a diazo phosphorus reagent ((1-diazo-2-oxo-propyl)-phosphonic acid dimethyl ester) in a potassium carbonate / methanol solution for converting the aldehyde group into an alkynyl group; performing de-protection of silicon with TBAF (Tetrabutylammonium Fluoride), and then performing ring closing in situ to generate 7-methoxyl-1-benzofuran; and obtaining the 7-methoxyl-1-benzofuran-4-formaldehyde through Vilsmeier aldehyde reaction. Compared with an existing reported preparation method, the preparation method provided by the invention has the advantages of cheap and easily obtained raw materials, less side reaction, high yield and simplicity and convenience in operation, and is beneficial for industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicine and relates to a new method for synthesizing 7-methoxyl-1-benzofuran-4-carbaldehyde. Background technique [0002] The 1-benzofuran skeleton is a common structure in natural products, and 7-methoxy-1-benzofuran-4-carbaldehyde is an important intermediate in organic synthesis, which is used in the synthesis of various drug precursors Wide range of applications. W.A.L.Otterlo (Tetrahedron, 2005, 61, 7746-7755) reported the synthesis of 7-methoxy-1-benzofuran-4-carbaldehyde by catalytic isomerization and ring-closing disproportionation of olefins, although the synthetic scheme is novel, but Due to the use of noble metal catalysts, the cost is extremely high, and the total yield is only 9%, so industrial production cannot be realized. [0003] Contents of the invention [0004] In order to solve the problems of high price and low yield in the prior art, the invention provides a method for synt...

Claims

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Application Information

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IPC IPC(8): C07D307/86C07F7/18
CPCY02P20/55C07D307/86C07F7/1804
Inventor 马军礼
Owner 天津羲泽润科技有限公司