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(E)-3-(benzfuran-5-yl) acrylic ester compound, preparation method and application thereof

A technology of acrylates and benzofuran, applied in the field of preparation of 3-propionic acid, can solve the problems of "three wastes" discharge, harsh reaction conditions, cumbersome reaction operation and post-treatment process, etc.

Inactive Publication Date: 2010-03-10
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The above-mentioned method for synthesizing 3-(2,3-dihydrobenzofuran-5-yl)-propionic acid (II) has expensive raw materials, harsh reaction conditions, cumbersome reaction operations and post-treatment processes, and partial yields. Low, serious discharge of "three wastes" in the preparation process, etc., make the synthesis cost of compound (II) higher, and the large-scale preparation is limited

Method used

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  • (E)-3-(benzfuran-5-yl) acrylic ester compound, preparation method and application thereof
  • (E)-3-(benzfuran-5-yl) acrylic ester compound, preparation method and application thereof
  • (E)-3-(benzfuran-5-yl) acrylic ester compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Preparation of 2-(4-bromophenoxy)-diethylacetal (2a)

[0045] Add 50.0g (0.29mol) of p-bromophenol, 62.6g (0.32mol) of bromoacetal, anhydrous K 2 CO 3 48.03g (0.35mol) and 500ml of acetone, heated and refluxed and stirred for 18h. After the reaction, filtered, the filtrate was evaporated to remove the solvent under reduced pressure, and the residual oil was dissolved in 500ml of chloroform. NaCl aqueous solution 100ml washed, the organic layer was washed with anhydrous NaCl 2 SO 4 Dry, filter, and evaporate the solvent under reduced pressure to obtain 77.15 g of 2-(4-bromophenoxy)-diethyl acetal, with a yield of 92.0%.

Embodiment 2

[0047] Preparation of 2-(4-bromophenoxy)-acetaldehyde (2b)

[0048]The operation process is the same as in Example 1, except that bromoacetal is replaced by 40% aqueous solution of chloroacetaldehyde, and acetone is replaced by N,N-dimethylformamide to obtain 2-(4-bromophenoxy)-ethyl Aldehyde, yield 83.9%.

Embodiment 3

[0050] Preparation of 5-bromobenzofuran (3)

[0051] Add 28.92g (0.1mol) of 2-(4-bromophenoxy)-diethyl acetal, 30.0g polyphosphoric acid, and 200ml 1,2-dichloroethane into the reaction flask, heat up and reflux and stir for 5h, After the reaction is over, add 100ml of ice water, stir evenly, separate the organic layer, wash with 10% aqueous sodium carbonate solution 50ml, saturated NaCl aqueous solution 25ml successively, and wash the organic layer with anhydrous NaCl 2 SO 4 Dry, filter, and distill under reduced pressure to obtain 16.82 g of light yellow 5-bromobenzofuran liquid, with a yield of 85.3%. 1 H NMR (CDCl 3 , 400MHz) δ: 7.75 (s, 1H, Ar-H 4 ), 7.64 (d, J=2.0Hz, 1H, Ar-H 2 ), 7.41 (d, J=8.8Hz, 1H, Ar-H 6 ), 7.39 (d, J=8.8Hz, 1H, Ar-H 7 ), 6.74 (d, J=2.0Hz, 1H, Ar-H 3 ); 13 C NMR (CDCl 3 , 100MHz) δ: 153.6 (Ar-C 7a ), 146.2 (Ar-C 2 ), 129.2 (Ar-C 3a ), 127.0 (Ar-C 6 ), 123.8 (Ar-C 4 ), 115.6 (Ar-C 5 ), 112.8 (Ar-C 7 ), 106.2 (Ar-C 3 ).

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Abstract

The invention discloses an (E)-3-(benzfuran-5-yl) acrylic ester compound (I), a preparation method of the compounds and an application thereof in preparing 3-(2, 3-dihydrobenzofuran-5-yl)-propionic acid. R represents straight-chain alkyl, or branched chain alkyl or naphthenic base of C1-C12, phenmethyl, substituted benzyl, allyl, aryl of C6-C10 and substituted aryl.

Description

technical field [0001] The present invention relates to (E)-3-(benzofuran-5-yl)acrylic acid ester compound (I), its preparation method and preparation 3-(2,3-dihydrobenzofuran-5-yl)- Application of propionic acid (II). [0002] [0003] (R stands for C 1-12 straight-chain or branched-chain alkyl or cycloalkyl, benzyl, substituted benzyl, allyl, C 6- 10 aryl, substituted aryl). Background technique [0004] 3-(2,3-Dihydrobenzofuran-5-yl)-propionic acid (II) is an important intermediate in the synthesis of selective melatonin receptor agonist - Ramelteon (Ramelteon), literature: J Med Chem 2002, 45(19), 4222; WO2006030739; WO 2008150953; WO 2008151170, etc., describe the preparation method of this compound, and these methods all start with 2,3-dihydrobenzofuran-5-carbaldehyde The raw material is further reduced after extending the carbon chain by different methods to obtain 3-(2,3-dihydrobenzofuran-5-yl)-propionic acid (II), and its reaction formula is as follows: [...

Claims

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Application Information

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IPC IPC(8): C07D307/79
Inventor 邓勇吴成龙沈怡万杰
Owner SICHUAN UNIV
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