Synthesis of N-heteroaryl(trifluoromethyl)hydroxyalkanoic acid esters by highly efficient solid acid-catalyzed hydroxyalkylation of indoles and pyrroles with activated trifluoromethyl ketones

Document Type

Article

Publication Date

11-2005

Department

Department of Chemistry

Abstract

The synthesis of N-heteroaryl(trifluoromethyl)hydroxyalkanoic acid esters by solid acid-catalyzed Friedel-Crafts hydroxyalkylation of indoles and pyrroles with ethyl 3,3,3-trifluoropyruvate and ethyl 4,4,4-trifluoroacetoacetate is described. The inexpensive and readily available K-10 montmorillonite is found to be an efficient catalyst for the synthesis of a wide variety of trifluoromethylated indol-3-yl- and pyrrol-2-yl-hydroxypropionic and -butanoic acid esters. Using a series of substituted indoles and pyrroles the corresponding products were isolated in excellent yield (up to 98%) and 100% selectivity under mild experimental conditions, during very short reaction times. Beyond these, the ease of product isolation, catalyst stability and handling make this process an attractive, environmentally benign alternative for the synthesis of the target compounds.

Publisher's Statement

© 2005 Wiley-VCH Verlag GmbH & Co. KGaA. Publisher’s version of record: https://doi.org/10.1002/adsc.200505117

Publication Title

Advanced Synthesis and Catalysis

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