A preparation of trifluorolactic aldehyde

Article abstract of DOI:10.1016/S0040-4020(99)00498-6

A five-step preparation of 2-benzoyloxy-333-trifluoropropanal from 1,2- epoxy-3,3,3-trifluoropropane via Pummerer rearrangement is described. The total yield of the aldehyde from the epoxide was 90%. The aldehyde kept its optical purity when it was in hydrate form, but it was found to readily racemize in its formyl form. The utilization of selenium instead of sulfur in these procedures offered advantages in controlled oxidation of the heteroatom for Pummerer rearrangement and the subsequent hydrolysis of Pummerer product, an aldehyde equivalent.