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Preparation method of alpha-acetyl substituted alpha, beta-unsaturated ester

An acyl-substituted and unsaturated technology, which is applied in the preparation of carboxylic acid esters, chemical instruments and methods, and the preparation of organic compounds, can solve problems such as difficult to meet environmental friendliness and environmental pollution, and achieve non-flammable and explosive safety , less environmental pollution, easy to operate and handle

Inactive Publication Date: 2007-04-18
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In recent years, we are committed to the research of clean production synthesis technology, and the synthesis of α-acyl substituted-α, β-unsaturated esters is one of our research contents. In the above-mentioned reported methods, it is difficult to meet the requirements of environmental friendliness. There are disadvantages of environmental pollution

Method used

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  • Preparation method of alpha-acetyl substituted alpha, beta-unsaturated ester
  • Preparation method of alpha-acetyl substituted alpha, beta-unsaturated ester
  • Preparation method of alpha-acetyl substituted alpha, beta-unsaturated ester

Examples

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Embodiment 1

[0019] The synthesis of embodiment 1α-acetyl group-beta-phenyl acrylate ethyl ester

[0020] Add ethyl acetoacetate (13g, 0.10mol), benzaldehyde (10.6g, 0.1mol), proline (10mmol) and 1-butyl-3-methylimidazolium tetrafluoroboron successively in a 100mL single-necked round bottom flask Salt ionic liquid 10ml, stirred at room temperature for 12h, stopped the reaction with saturated ammonium chloride solution, extracted with ethyl acetate, separated the organic layer, separated and purified to obtain 18.5g of the product, with a yield of 85%. The aqueous layer was extracted with dichloromethane, and the solvent was evaporated to obtain 1-butyl-3-methylimidazolium tetrafluoroborate ionic liquid, which was recycled for use.

Embodiment 2

[0021] The synthesis of embodiment 2α-acetyl group-β-phenyl acrylate ethyl ester

[0022] Add ethyl acetoacetate (13g, 0.10mol), benzaldehyde (10.6g, 0.1mol), glycine (10mmol) and 1-butyl-3-methylimidazole tetrafluoroborate successively in a 100mL single-necked round bottom flask 10ml of ionic liquid was stirred and reacted at room temperature for 10h. The reaction was terminated with saturated ammonium chloride solution, extracted with ethyl acetate, and the organic layer was separated, separated and purified to obtain 20.1g of the product with a yield of 92.2%. The aqueous layer was extracted with dichloromethane, and the solvent was evaporated to obtain 1-butyl-3-methylimidazolium tetrafluoroborate ionic liquid, which was recycled for use.

Embodiment 3

[0023] The synthesis of embodiment 3α-acetyl group-beta-phenyl acrylate ethyl ester

[0024] Add ethyl acetoacetate (13g, 0.10mol), benzaldehyde (10.6g, 0.1mol), threonine (10mmol) and 1-butyl-3-methylimidazolium tetrafluoroboron successively in a 100mL single-necked round bottom flask Salt ionic liquid 10ml, stirred at room temperature for 14h, stopped the reaction with saturated ammonium chloride solution, extracted with ethyl acetate, separated the organic layer, separated and purified to obtain 19.2g of the product, with a yield of 88%. The aqueous layer was extracted with dichloromethane, and the solvent was evaporated to obtain 1-butyl-3-methylimidazolium tetrafluoroborate ionic liquid, which was recycled for use.

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Abstract

The present invention relates to a method for synthesizing alpha-acyl substituted alpha, beta-unsaturated ester. Said method is characterized by including the following steps: under the catalytic action of amino acid making acyl-substituted acetate and aldehyde produce reaction in an ionic solution, after the reaction is completed, making separation and purification so as to obtain the invented product alpha-acyl substituted alpha, beta-unsaturated ester.

Description

(1) Technical field [0001] The invention relates to a synthesis method of α-acyl substituted α, β-unsaturated ester. (2) Background technology [0002] α-acyl substituted α, β-unsaturated esters are an important class of functional intermediates in organic synthesis, as shown in formula (V). The reaction substrate can be used as a dienophile in the Diels-Alder reaction, a diene in the Hetero Diels-Alder reaction, and an acceptor in the Michael addition reaction. Due to the existence of acyl and carboxyl carbon-oxygen bonds shown in the formula, Lewis acid is easy to form bidentate coordination with acyl and carboxyl carbon-oxygen bonds, which is beneficial to the control of the reaction surface. After the reaction, the acyl group and carboxyl group are easily removed, and functional group conversion reactions can also be carried out according to their chemical characteristics to synthesize functional chiral compounds. For example, under the catalysis of chiral catalysts, t...

Claims

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Application Information

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IPC IPC(8): C07C69/738C07C67/347B01J31/02
Inventor 裴文王永江
Owner ZHEJIANG UNIV OF TECH
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