茚草酮的合成工艺改进

Improved synthesis of indanofan

本论文以价廉易得的间氯苯乙酮为起始原料,经与甲基氯化镁加成、对甲苯磺酸脱水、N-氯代丁二酰亚胺氯代3步反应制得1-氯-3-(3-氯丙基-1-烯-2-基)苯(5);以邻苯二甲酸二乙酯为原料,经与丁酸乙酯环合制得2-乙基-1H-茚-1,3(2H)-二酮(7),7再与中间体5发生取代反应后经间氯过氧苯甲酸氧化制得终产物茚草酮(1),总收率47%(以2计),纯度99.77%。该路线反应原料廉价易得,反应条件温和、操作简便,适合工业化生产。

By using inexpensive and readily available m-chloroacetophenone,1-chloro-3-(3-chloroprop-1-en-2-yl)benzene(5)was synthesized via 3 steps through methylmagnesium chloride addition,dehydration with p-toluenesulfonic acid and chlorination with N-chlorosuccinimide.On the other hand,2-ethyl-1H-indene-1,3(2H)-dione(7)was synthesized by cyclization of diethyl phthalate with ethyl butyrate,and then underwent substitution with intermediate 5 and further oxidation with m-chloroperoxybenzoic acid to provid the final product indanofan.The total yield was 47%(based on 2)and the purity was 99.77%.With the advantages of easy availability of raw materials,mild condition,easy to handle,this route was suitable for the industrial production.