Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2000; 2000(8): 1078-1080
DOI: 10.1055/s-2000-6320
DOI: 10.1055/s-2000-6320
short paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.
Preparation of 4-Hydroxy-2-trifluoromethylthiophene: A Novel Bioisostere of α,α,α-Trifluoro-m-cresol
Further Information
Publication History
Publication Date:
31 December 2000 (online)
A simple and convenient four-step synthesis of 4-hydroxy-2-trifluoromethylthiophene (1) a novel bioisostere of α,α,α-trifluoro-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 quantities of 1 have been obtained utilizing the present procedure.
addition-reactions - cyclizations - thiophenes - Fiesselmann reaction - bioisosteres