Reaction of ethyl 4,4,4-trifluoroacetoacetate enolate with 3-bromo-1,1,1-trifluoroacetone: Synthesis of 2,4-bis (trifluoromethyl) furan

Article abstract of DOI:10.1016/S0022-1139(96)03518-X

The potassium enolate of ethyl 4,4,4-trifluoroacetoacetate 1 reacts with 3-bromo-1,1,1-trifluoroacetone 2 in DMSO solution to yield three products. Ethyl 2,4-bis(trifluoromethyl)-4-hydroxydihydro-3-furoate 3 is generated via C-acylation. The hydrated trifluoromethyl ketone 4 is formed by O-alkylation and 4 reacts further with 2 to give the di-O-alkylated ketone hydrate 5. Compound 3 undergoes dehydration to the furan derivative 6 on reaction with Ac₂O-ZnCl₂.