A new bis(2,2,2-trifluoroethyl)phosphonate for the synthesis of Z-unsaturated N-methoxy-N-methylamides

Samuel Fortin; Félix Dupont; Pierre Deslongchamps

doi:10.1021/jo025816s

A new bis(2,2,2-trifluoroethyl)phosphonate for the synthesis of Z-unsaturated N-methoxy-N-methylamides

J Org Chem. 2002 Jul 26;67(15):5437-9. doi: 10.1021/jo025816s.

Authors

Samuel Fortin¹, Félix Dupont, Pierre Deslongchamps

Affiliation

¹ Département de chimie, Institut de pharmacologie, Université de Sherbrooke, 3001 12e Avenue Nord, Sherbrooke, Québec J1H 5N4, Canada.

PMID: 12126448
DOI: 10.1021/jo025816s

Abstract

The N-methoxy-N-methyl bis(2,2,2-trifluoroethyl)phosphonamide was easily obtained via the Arbuzov reaction with use of commercially available tris(2,2,2-trifluoroethyl)phosphite, 2-bromo-N-methoxy-N-methylacetamide, and KF/alumina. The reaction of bis(2,2,2-trifluoroethyl)phosphonate with several aldehydes demonstrates the versatility of the method, which gives Z-unsaturated amides in good yields.