Imidazole → 4-(t-Butyldimethylsilyloxy)indole

Participants

Reaction Steps

To a solution of 1H-indole-4-ol (2.4 g) in DMF (50 mL) was added tert-butyldimethylchlorosilane (2.7 g) and 1H-imidazole (1.5 g) at ambient temperature. The reaction mixture was stirred for 17 hours at ambient temperature. The resulting mixture was evaporated in vacuo and diluted with EtOAc. The organic layer was washed with water and brine and then dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silicagel column chromatography (n-hexane:EtOAc=80:20-60:40) to give 4-{[tert-butyl(dimethyl)silyl]oxy}-1H-indole.

Provenance & Evidence