1-Benzyl-2-ethyl-4-methoxy-1H-indole → 1-Benzyl-2-ethyl-1H-indol-4-OL

Participants

Reaction Steps

A solution of 3.1 g (11.7 mmol) of 2-ethyl-4-methoxy-1-(phenylmethyl)-1H-indole and 48.6 mL of 1M BBr3/CH2Cl2 in 50 mL of methylene chloride is stirred at room temperature for 5 hours and concentrated at reduced pressure. The residue is dissolved in ethyl acetate, washed with brine and dried (MgSO4). After concentrating at reduced pressure, the residue is chromatographed on silica gel eluting with 20% EtOAc/hexane to give 1.58 g (54% yield) of 2-ethyl-4-hydroxy-1-(phenylmethyl)-1H-indole, mp, 86-90° C.

Provenance & Evidence