Imidazole → HCID 157380137, compound

Participants

Reaction Steps

To a solution of indole-1-methanol (Combi-Blocks, 1.0 g, 6.8 mmol) in 50 mL of dichloromethane was added imidazole (0.56 g, 8.2 mmol) followed by tert-butyldimethylsilyl chloride (1.1 g, 7.0 mmol). The mixture was stirred at ambient temperature for 17 hours then 10 mL H2O was added and the layers were separated. The aqueous layer was extracted 3×5 mL of dichloromethane and the combined organic extracts were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via flash column chromatography (SiO2, 80% hexanes in EtOAc) to provide the title compound (1.6 g, 6.2 mmol, 91% yield). MS (DCI/NH3) m/z 262 (M+H)+.

Provenance & Evidence