Wittig反应在α,β⁃不饱和羧酸酯合成中的应用

doi:10.3969/j.issn.1672-6952.2020.03.005

辽宁石油化工大学学报 ›› 2020, Vol. 40 ›› Issue (3): 24-27.DOI: 10.3969/j.issn.1672-6952.2020.03.005

Wittig反应在α,β⁃不饱和羧酸酯合成中的应用

赵世晨¹，马金波²，于芳¹

1.辽宁石油化工大学化学化工与环境学部，辽宁抚顺 113001； 2.沈阳市环境监测中心站，辽宁沈阳 110000

收稿日期:2019-04-30 修回日期:2019-10-14 出版日期:2020-06-29 发布日期:2020-07-06
通讯作者: 于芳 (1984⁃)，女，博士，副教授，从事过渡金属催化的有机合成方面的研究；E⁃mail：yufang1112002@163.com。
作者简介:赵世晨 (1994?)，男，硕士研究生，从事有机合成方面的研究；E?mail：zsc12202118 @163.com。
基金资助:
国家自然科学基金项目(1402078)。

Application of Wittig Reaction in Synthesis of α,β⁃Unsaturated Carboxylic Esters

Zhao Shichen¹， Ma Jinbo²， Yu Fang¹

1.College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Fushun Liaoning 113001, China； 2.Shenyang Environmental Monitoring Center, Shenyang Liaoning 110000, China

Received:2019-04-30 Revised:2019-10-14 Published:2020-06-29 Online:2020-07-06

摘要/Abstract

摘要： 以溴乙酸甲酯和三苯基膦为起始原料，首先制备溴磷盐，再加入碱，顺利地制得了Wittig试剂。利用苯甲醛和Wittig试剂发生Wittig反应制得α,β⁃不饱和羧酸酯（肉桂酸甲酯）。结果表明，最佳反应条件为：Wittig试剂和苯甲醛作为原料，苯作为溶剂，同时加入碳酸钾作为添加剂，在常温下搅拌反应24 h，以较高的收率（86%）得到了最终产物肉桂酸甲酯。同时，产物的构型为反式烯烃，说明了此方法具有较好的立体选择性。

关键词: Wittig试剂, 　Wittig反应, 　α,β?不饱和羧酸酯, 　肉桂酸甲酯

Abstract: In this paper, methyl bromoacetate and triphenylphosphine were used as starting materials. First, bromophosphorus salt was prepared, and then alkali was added to prepare Wittig reagent. Preparation of α,β⁃unsaturated carboxylic acid ester (methyl cinnamate) by Wittig reaction using benzaldehyde and Wittig reagent The results show that the optimal conditions for the reaction are: Wittig reagent and benzaldehyde are used as raw materials, benzene is used as a solvent, and potassium carbonate is added as an additive. The reaction is stirred at room temperature for 24 hours, and the final product methyl cinnamate is obtained in a higher yield (86%). At the same time, the configuration of the product is a trans olefin product, indicating that the method has good stereoselectivity.

Key words: Wittig reagent, Wittig reaction, α,β?Unsaturated carboxylic acid ester, Methyl cinnamate

赵世晨, 马金波, 于芳. Wittig反应在α,β⁃不饱和羧酸酯合成中的应用[J]. 辽宁石油化工大学学报, 2020, 40(3): 24-27.

Zhao Shichen, Ma Jinbo, Yu Fang. Application of Wittig Reaction in Synthesis of α,β⁃Unsaturated Carboxylic Esters[J]. Journal of Liaoning Petrochemical University, 2020, 40(3): 24-27.

Wittig反应在α,β⁃不饱和羧酸酯合成中的应用

Application of Wittig Reaction in Synthesis of α,β⁃Unsaturated Carboxylic Esters

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