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Communication | Regular issue | Vol 27, No. 8, 1988, pp.1855-1860
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4616
The Friedel-Crafts Acylation of Ethyl Pyrrole-2-carboxylate. Scope, Limitations, and Application to Synthesis of 7-Substituted Indoles

Yasuoki Murakami,* Masanobu Tani, Takahiro Ariyasu, Chika Nishiyama, Toshiko Watanabe, and Yuusaku Yokoyama

*School of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan

Abstract

The Friedel-Crafts acylation of ethyl pyrrole-2-carboxylate (3) was studied under a variety of conditions using various Lewis acids and acyl chlorides. The acylation with some Lewis acids such as BF3 OEt2 gave a mixture of 4- and 5-acyl derivatives (5 and 6), whereas the acylation with various acyl chlorides in the presence of AlCl3 gave exclusively 4-acyl derivatives (5). Acylation in this experiment was applied to a new methodology for synthesis of 7-substituted indoles.