3,4,4-Trifluoro-3-butenoyl chloride → HCID 21836481, compound

Participants

Reaction Steps

To a solution of 3,4,4-trifluoro-3-butenoyl chloride (3.75 g, 23.65 mmol) in anhyd. ether (100 mL) was treated with copper(I)iodide (2.28 g, 12 mmol) followed by 24 mL of 1.0 M solution of benzylmagnesium chloride in ether dropwise at -78° C. with stirring under nitrogen. The reaction mixture was stirred at -78° C. for 10 min and allowed to reach to r.t and filtered. The filtrate was successively washed with 2N HCl, 5% sodium bicarbonate and brine, and dried. The residue, a mixture of several products, obtained after evaporation of the solvent was chromatographed over silica gel (20% hexanes in dichloromethane) and the major product (least polar) was isolated and further purified by kugelrohr distillation, b.p. 130-140° C. (pot temperature)/12 mmHg. Proton and fluorine NMR spectra of this material was found to correspond to the title compound.

Provenance & Evidence