Ethyl 5-(phenylmethoxy)-1H-indole-2-carboxylate → Ethyl 5-hydroxy-1H-indole-2-carboxylate

Participants

Reaction Steps

A solution of 5-benzyloxyindole-2-carboxylic acid ethyl ester (10 g, 34 mmol) in 250 mL of ethanol was treated with 10% Pd/C and hydrogenated under atmospheric pressure (double-walled balloon) for 20 h. The reaction mixture was diluted with EtOAc and filtered through Celite®. Evaporation of the filtrate in vacuo gave the title compound as a tan solid (7 g, 99%). 1H NMR (400 MHz, CDCl3) δ 8.86 (br s, 1H), 7.29 (d, J=8.80 Hz, 1H), 7.11 (s, 1H), 7.06 (s, 1H), 6.94 (d, J=8.70 Hz, 1H), 4.83 (br s, 1H), 4.42 (q, J=7.09 Hz, 2H), 1.41 (t, J =7.08 Hz, 3H).

Provenance & Evidence