Tetrabutylammonium Fluoride → Ethyl 6-(3,5-difluoro-4-hydroxybenzyl)-8-[5-fluoro-2-(4'-trifluoromethylbiphenyl-4-ylmethoxy)-phenyl]oct-7-enoate

Participants

Reaction Steps

720 mg (0.89 mmol) of ethyl 6-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-8-[5-fluoro-2-(4′-trifluoromethylbiphenyl-4-ylmethoxy)phenyl]oct-7-enoate are introduced into 15 ml of THF at 0° C. under argon, 1.77 ml (1.77 mmol) of a 1 M solution of tetra-n-butylammonium fluoride in THF are added, and the mixture is stirred at room temperature until reaction is complete. All the volatile components are removed in vacuo. The resulting crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:1). 400 mg (68% of theory) of the title compound are obtained as an E/Z mixture (2:1).

Provenance & Evidence