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

Participants

Reaction Steps

3.1 g (11.7 mmol) of 2-ethyl-4-methoxy-1-(phenylmethyl)-1H-indole is O-demethylated by treating it with 48.6 mL of 1M BBr3/CH2Cl2, then stirred at room temperature for 5 hours and concentrated at reduced pressure. The residue is dissolved in ethyl acetate, then washed with brine and dried. The reaction product is then chromatographed on silica gel (eluted 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