Acetic Acid → HCID 86742613, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl E-3-(4-ethoxyphenyl)-4,4,4-trifluorobut-2-enoate, prepared according to Example 17, stage 1, (1.5 g, 5.5×10-3 moles) in toluene (20 ml) at -78° C. was added dropwise one molar equivalent of diisobutylaluminium hydride (5.5 ml, 5.5×10-3 moles) in toluene. The resulting solution was stirred at -78° C. for two hours before quenching the reaction by the sequential addition of acetic acid (0.40 ml, 7.0×10-3 moles), water (1 ml) and sodium sulphate (10 g). The resulting slurry was allowed to warm to room temperature and after a further twenty minutes stirring the solids were filtered off through silica. After removal of the solvent the crude aldehyde was purified by silica chromatography (eluted with 10%, in petroleum ether to give the title compound (0.87 g, 65%).

Provenance & Evidence