3-氧代四氢噻吩-4-羧酸甲酯的合成工艺优化  

The Process Optimization on Synthesis of 3-Keto-4-carbomethoxythiophane

作　　者：谭春斌[1] 刘晓玲[1] 方艾权[1] 杜洪飞[1] Tan Chunbin;Liu Xiaoling;Fang Aiquan;Du Hongfei(Chongqing Academy of Chinese Materia Medica,Chongqing 40006)

机构地区：[1]重庆市中药研究院,重庆400065

出　　处：《化学通报》2018年第10期957-959,共3页Chemistry

摘　　要：以甲醇与巯基乙酸为起始原料合成了3-氧代四氢噻吩-4-羧酸甲酯(Ⅲ),产物结构通过~1H NMR、^(13)C NMR、HRMS等表征。考察了无机碱(NaHCO_3、Na_2CO_3、K_2CO_3、NaOH、KOH)与有机碱(乙胺、三乙胺、吡啶、甲醇钠、甲醇钾)和不同溶剂以及温度对合成3-氧代四氢噻吩-4-羧酸甲酯收率的影响。结果表明,有机碱效果优于无机碱;甲苯为较优溶剂;高温反应有利于Ⅲ的合成。合成化合物Ⅲ的较优工艺为:甲苯作溶剂,吡啶为碱催化剂,在80℃下反应2h,收率可达78%。3-Keto-4-carbomethoxythiophane（Ⅲ） was synthesized by Dieckmann cyclization reaction,using methanol and mercapto acetic acid as the starting materials. The structure of the product was confirmed by ^1H NMR,^13C NMR and HRMS. Effects of different organic or inorganic base types,reaction solvent and temperature on the cyclization reaction were investigated as well. The results showed that organic bases are superior to inorganic bases; high temperature is beneficial to give Ⅲ. The optimized process for the synthesis of compound III is as follows： pyridine as base,toluene as solvent,react at 80℃ for 2 h. The yield of 3-Keto-4-carbomethoxythiophane reached 78%.

关 键 词：3-氧代四氢噻吩-4-羧酸甲酯 丙烯酸甲酯 巯基乙酸甲酯 工艺优化 

分 类 号：TQ251.2[化学工程—有机化工]