4-Methoxybenzaldehyde → HCID 66930896, compound

Participants

Reaction Steps

To a suspension of 6-phenoxyhexyltriphenylphosphonium bromide (6.1) (4.60 g, 8.86 mmol) in dry THF (80 mL) at 0° C., under an argon atmosphere was added potassium bis(trimethylsilyl)amide (1.76 g, 8.86 mmol). The resulting slurry was stirred for 5 min at the same temperature and then a solution of 4-methoxybenzaldehyde (0.61 g, 4.46 mmol) in dry THF (10 mL) was added. The reaction mixture was stirred for an additional 10 min and quenched with saturated aqueous NH4Cl (20 mL). The resulting mixture was warmed to room temperature, diluted with Et2O (100 mL), the organic phase was separated and the aqueous phase extracted with Et2O. The combined organic layer was washed with brine, dried over MgSO4 and the solvent evaporated under reduced pressure. The residue obtained was purified through a short column of silica gel, eluting with 5% Et2O-hexane, to give the product 7.1 (1.21 g, 92% yield, predominantly cis, cis:trans=96:4) as a colorless liquid.

Provenance & Evidence