Synthesis and reactions of bis(2,2,2-trifluoroethyl)-ß-ketophosphonates

Abstract

The research contained herein is focused on a previously unreported synthesis of bis(2,2,2-trifluoroethoxy)-β-ketophosphonates via the hydration of the corresponding bis(2,2,2-trifluoroethoxy) alkynylphosphonates. The first step was to prepare all starting materials, namely the bis(2,2,2-trifluoroethyl) alkynylphosphonates from the corresponding commercially available terminal alkynes and bis(2,2,2-trifluoethoxy) phosphorochloridate. The hydration of the bis(2,2,2-trifluoroethoxy) alkynylphosphonates to yield the desired products was accomplished using mercury sulfate and 10% sulfuric acid. 2,2,2-Trifluoethanol was used as the solvent. The use of these β-keto phosphonates in the Horner-Wadsworth-Emmons reaction was also examined.