Imidazole → HCID 53821858, compound

Participants

Reaction Steps

A solution of tert-butyldiphenylsilyl chloride (850 mg, 3.09 mmol) in dichloromethane (10 cm3+5 cm3 rinse) was added to a stirred solution of benzyl 4-benzyloxy-3-hydroxybenzoate (827 mg, 2.47 mmol) and imidazole (421 mg, 6.18 mmol) in dichloromethane (15 cm3). After a few minutes a precipitate formed. The mixture was stirred overnight under an atmosphere of nitrogen, then was poured into water (50 cm3) The layers were shaken and separated, then the aqueous phase was further extracted with dichloromethane (2×50 cm3). The combined extracts were washed with brine (50 cm3) and evaporated to a pale yellow oil. This was filtered through a short silica column and eluted with 20% ethyl acetate in petroleum ether. Evaporation of the filtrate gave benzyl 3-(tert-butyldiphenylsilyloxy)-4-benzyloxybenzoate (1.646 g) as a very pale yellow oil, containing some tert-butyldiphenyl-silanol, which was used directly for the next step.

Provenance & Evidence