Imidazole → 3-[(Tert-butyldimethylsilyl)oxy]phenol

Participants

Reaction Steps

To a solution of resorcinol (1.0 g, 0.9 mmol) and tert-butyldimethylsilyl chloride (1.4 g, 0.9 mmol) in 5 mL of dry DMF was gradually added imidazole (1.2 g, 1.8 mmol) and the solution was stirred for 1 hour. TLC analysis (silica gel, 20% ethyl acetate/hexane) showed completion of reaction. The solution was poured into 25 mL of water and extracted with 3×25 mL of ether. The combined ether solutions were dried over anhydrous MgSO4. Evaporation of solvent gave an oil which was chromatographed on silica using 20% ethyl acetate/hexane to give the product as a white solid in 70% yield: 1H NMR (CDCl3) δ0.199 (s, 6H), 0.983 (s, 9H), 6.39-7.09 (m, 4H).

Provenance & Evidence