Benzaldehyde → [4-(tert-Butyldimethylsilanyloxymethyl)-3-methoxyphenyl]-phenylmethanol

Participants

Reaction Conditions

Reaction Steps

To 2-(tert-Butyldimethylsilanyloxymethyl)-5-bromoanisole (500 mg, 1.51 mmol) in THF (10 ml) at -78° C. was added n-BuLi (1.13 ml of a 1.6M solution in penthane, 1.81 mmol) and the mixture allowed to stir for 1 h at -78° C. Benzaldehyde (176 mg, 1.66 mmol) was added and the mixture allowed to warm to room temperature and stirred for 1 h. Water (20 ml) was added and the mixture extracted with ether (3×10 ml). The combined extracts were washed with water (10 ml), brine (10 ml), dried (Na2SO4) and evaporated under reduced pressure. The resulting residue was purified by chromatography (SiO2, 50% ether/petrol) to give the title compound as a colourless oil (303 mg, 56%).

Provenance & Evidence