Preparation of 4-hydroxy-2-trifluoromethylthiophene: a novel bioisostere of α, α, α-trifluoro-m-cresol

GM Karp, D Samant, S Mukhopadhyay, ME Condon…

Index: Karp, Gary M.; Samant, Dilip; Mukhopadhyay, Sudarsan; Condon, Michael E.; Kleemann, Axel Synthesis, 2000 , # 8 p. 1078 - 1080

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Citation Number: 13

Abstract

Abstract: A simple and convenient four-step synthesis of 4-hydroxy-2- trifluoromethylthiophene (1) a novel bioisostere of a, a, atrifluoro-m-cresol is reported. The key step is the condensation between ethyl 3-methoxy-4, 4, 4-trifluorocrotonate and methyl thioglycolate to form methyl 3-hydroxy-5-trifluoromethylthiophene-2-carboxylate (6). Hydrolysis of the ester followed by decarboxylation furnishes 1. Multi-hundred gram ...