Synlett
DOI: 10.1055/s-0036-1589097
letter
© Georg Thieme Verlag Stuttgart · New York

4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO), a Versatile Precursor for Trifluoromethyl-Substituted Heteroarenes – a Short Synthesis of Celebrex® (Celecoxib)

Heiko Sommera, Max Braunb, Benjamin Schrödera, Andreas Kirschning*a
  • aInstitut für Organische Chemie und Biomolekulares Wirkstoffzentrum (BMWZ) der Leibniz Universität Hannover, Schneiderberg 1B, 30167 Hannover, Germany   Email: andreas.kirschning@oci.uni-hannover.de
  • bSolvay Fluor GmbH, Hans-Böckler-Allee 20, 30173 Hannover, Germany
The work was funded by the Deutsche Forschungsgemeinschaft (Cluster of Excellence REBIRTH; ‘From Regenerative Biology to Reconstructive Therapy’ EXC 62).
Further Information

Publication History

Received: 14 July 2017

Accepted after revision: 17 July 2017

Publication Date:
22 August 2017 (eFirst)

Abstract

4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO) serves as a trifluoromethyl-containing building block for the preparation of trifluoromethyl-substituted thiophenes, furans, pyrrols, and piperazines. Key steps are an addition–elimination reaction to ETFBO followed by the thiazolium-catalyzed Stetter reaction. The scope of this chemistry was demonstrated in a new synthetic approach towards the COX-2 selective, nonsteroidal anti-inflammatory drug Celebrex® (celecoxib).

Supporting Information