4-Hydroxybenzaldehyde → 4-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehyde

Participants

Reaction Steps

to a stirred solution of 4-hydroxybenzaldehyde (25.0 g, 205 mmol) in dry DMF (200 mL) was added imidazole (28.0 g, 410 mmol) and TBDMS-Cl (32.4 g, 215 mmol) under an argon atmosphere. The resulting mixture was stirred for 4 h at room temperature (rt) then water was added and the mixture was extracted with ether (2×300 mL) and dichloromethane (2×300 mL). The combined organics were dried (MgSO4), filtered and concentrated under vacuum. The crude oil was purified by filtration through silica gel (eluting with hexane-EtOAc, 95:5) to give the product as a colourless oil (48.0 g, 99%).

Provenance & Evidence