Imidazole → 6-((tert-butyldimethylsilyl)oxy)-1H-indole

Participants

Reaction Steps

A mixture of 5.5 g 6-hydroxyindole, 7.47 g tert-butyldimethylsilyl chloride, 7.03 g imidazole, and 25 mL dimethylformamide is stirred at ambient temperature for 20 h. The reaction is diluted with ethyl acetate, washed with water (2×), dried (MgSO4), and the solvent removed under reduced pressure to provide an oil. The oil is chromatographed, eluting with ethyl acetate/heptane, to afford 9.05 g (88%) of 6-(tert-butyldimethylsiloxy)-1H-indole as a white solid: TLC Rf 0.4 (silica, 1:9 ethyl acetate/heptane).

Provenance & Evidence