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Method for preparing 2-furan formyl-3-aryl-4-ethoxycarbonyl-5-methyl-anti-form-2 and 3-dihydrofuran under catalytic action of niobium chloride

A technology for brominating furoyl methyl triphenylarsine and furoyl group is applied in the field of chemical raw material synthesis to achieve the effects of easy separation and purification, mild reaction conditions and high stereoselectivity

Inactive Publication Date: 2013-12-18
YICHUN JINYANG NEW MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] There is no report on the preparation of 2-furoyl-3-aryl-4-ethoxycarbonyl-5-methyl-trans-2,3-dihydrofuran by niobium pentachloride

Method used

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  • Method for preparing 2-furan formyl-3-aryl-4-ethoxycarbonyl-5-methyl-anti-form-2 and 3-dihydrofuran under catalytic action of niobium chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Prepare 2-furoyl-3-phenyl-4-ethoxycarbonyl-5-methyl-trans-2,3-dihydrofuran according to the following steps:

[0028] (a) Control the amount of furoylmethyltriphenylarsine bromide: 2-ethoxycarbonyl-3-phenyl-ethyl acrylate: niobium pentachloride: dichloromethane at a ratio of 1:1: 2:2;

[0029] (b) Put the ratio of the amount of each substance weighed in step (a) into the reaction container at the same time, stir until each component is fully dissolved, control the reaction temperature to 0 ~ 40 ℃, and the reaction time is 5 to 6 hours to obtain the reaction solution;

[0030] (c) Pour the reaction solution prepared in step (b) into cold water, crystallize and filter, and dry to obtain 2-furoyl-3-aryl-4-ethoxycarbonyl-5-methyl-resin Formula - 2,3-dihydrofuran.

[0031] The product yield of the obtained 2-furoyl-3-phenyl-4-ethoxycarbonyl-5-methyl-trans-2,3-dihydrofuran was 63%.

[0032] The obtained invention product is subjected to NMR detection, NMR data: 1 H NMR (...

Embodiment 2

[0034] This example prepares 2-furoyl-3-phenyl-4-ethoxycarbonyl-5-methyl-trans-2,3-dihydrofuran according to the following steps:

[0035] (a) Control the amount of furoylmethyltriphenylarsine bromide: 2-ethoxycarbonyl-3-phenyl-ethyl acrylate: niobium pentachloride: dichloromethane at a ratio of 1:2: 2:4;

[0036] (b) Put the ratio of the amount of each substance weighed in step (a) into the reaction container at the same time, stir until each component is fully dissolved, control the reaction temperature to 0-40 ℃, and the reaction time to 5-6 hours to get the reaction solution;

[0037] (c) Pour the reaction solution obtained in step (b) into cold water, crystallize and filter, and dry to obtain 2-furoyl-3-phenyl-4-ethoxycarbonyl-5-methyl-trans -2,3-dihydrofuran. The yield of the obtained 2-furoyl-3-phenyl-4-ethoxycarbonyl-5-methyl-trans-2,3-dihydrofuran was 73%.

[0038] The obtained invention product is subjected to NMR detection, NMR data: 1 H NMR (400 MHz, CDCl3 ) ...

Embodiment 3

[0040] Prepare 2-furoyl-3-phenyl-4-ethoxycarbonyl-5-methyl-trans-2,3-dihydrofuran according to the following steps:

[0041] (a) Control the amount of furoylmethyltriphenylarsine bromide: 2-ethoxycarbonyl-3-phenyl-ethyl acrylate: niobium pentachloride: dichloromethane at a ratio of 1:2: 2:4;

[0042] (b) Stir the furoylmethyltriphenylarsine bromide, 2-ethoxycarbonyl-3-phenyl-ethyl acrylate and dichloromethane to fully dissolve, then slowly add pentachloro Niobium chloride was reacted, the reaction temperature was controlled to be 0-40°C, and the reaction time was 3-4 hours to obtain a reaction solution;

[0043] (c), pour the reaction solution obtained in step (b) into cold water, crystallize and filter, and dry to obtain 2-furoyl-3-phenyl-4-ethoxycarbonyl-5-methyl- Formula - 2,3-dihydrofuran. The product yield of the obtained 2-furoyl-3-phenyl-4-ethoxycarbonyl-5-methyl-trans-2,3-dihydrofuran was 71%.

[0044] NMR data: 1 H NMR (400 MHz, CDCl 3 ) δ (ppm): 1.04 (t, J...

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Abstract

The invention provides a method for preparing 2-furan formyl-3-aryl-4-ethoxycarbonyl-5-methyl-anti-form-2 and 3-dihydrofuran under the catalytic action of niobium chloride. According to the method for preparing the 2-furan formyl-3-aryl-4-ethoxycarbonyl-5-methyl-anti-form-2 and 3-dihydrofuran under the catalytic action of the niobium chloride, the niobium chloride is used to serve as a catalyzer, and reaction is carried out under the reaction condition with low requirements to prepare the 2-furan formyl-3-aryl-4-ethoxycarbonyl-5-methyl-anti-form-2 and 3-dihydrofuran. The method for preparing the 2-furan formyl-3-aryl-4-ethoxycarbonyl-5-methyl-anti-form-2 and 3-dihydrofuran under the catalytic action of the niobium chloride has the advantages that the prepared product is easy to separate, the technique is simple, and little industrial waste is generated.

Description

technical field [0001] The invention relates to a method for synthesizing chemical raw materials, in particular to the catalytic preparation of 2-furoyl-3-aryl-4-ethoxycarbonyl-5-methyl-trans-2,3-dihydrofuran by niobium pentachloride Methods. technical background [0002] As a heterocyclic compound, dihydrofuran ring is closely related to human life. No matter in natural compounds or synthetic compounds, structural fragments of dihydrofuran can be found. For example, a large class of fungicides with important commercial value is based on 2,3-dihydrofuran as its basic skeleton. Moreover, the furan ring The modified nucleosides exhibit strong antiviral and antitumor effects. On the other hand, dihydrofuran derivatives are also very useful intermediates in organic synthesis, which can be further converted into many biologically active compounds, and many different compounds can be synthesized from them. Because dihydrofuran has a wide range of uses in chemistry, its synthesi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/46
Inventor 王常清易艳平
Owner YICHUN JINYANG NEW MATERIALS CO LTD
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