4-Methoxybenzaldehyde → 1'-Hydroxyestragole

Participants

Reaction Steps

To a solution of p-anisaldehyde (1.54 ml) in tetrahydrofuran (20 ml) at −10° C. under argon was added dropwise vinyl magnesium bromide (1 M in THF, 12.5 ml). The solution was stirred overnight at room temperature and quenched by addition of saturated aqueous ammonium chloride (20 ml). The organic phase was separated, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (SiO2, ethyl acetate:cyclohexan 7:3) to give 1.05 g of the desired product as a colorless oil (51%) which was characterized by its mass and NMR spectra.

Provenance & Evidence