Methyl 4-Formylbenzoate → 4-(Phenyl-1-butenyl)benzoic acid, methyl ester

Participants

Reaction Conditions

Reaction Steps

To a 0° solution of Part A (1) compound (3.55 g, 1.25 eq) in 30 ml of dry THF under Argon was added K-t-amylate (3.9 ml, 1.1 eq). After stirring for 30 minutes at 0° C. then allowing to warm to room temperature, a solution of methyl 4-formylbenzoate (1.0 g, 6.1 mmol, Fluka) in ~8 ml of dry THF was added dropwise. This solution was stirred for 3 hours at room temperature, then diluted with ~1 ml of H2O, and concentrated to remove most of the THF. EtOAc (18 200 ml) was added and the mixture was washed with H2O, 1N HCl (2X) and brine. After drying over anhydrous MgSO4 the solvent was removed in vacuo to yield a yellow oil which solidified. Column purification of this crude product on silica gel eluted with 95:5 hexane/EtOAc yielded after concentration title aldehyde 1.5 g (93%) as a clear oil.

Provenance & Evidence