5-Benzyloxy-1-isopropyl-1H-indole-2-carboxylic acid → 5-Hydroxy-1-isopropyl-1H-indole-2-carboxylic acid

Participants

Reaction Steps

A mixture of 5-benzyloxy-1-isopropyl-1H-indole-2-carboxylic acid (41.6 g, 1.0 eq.) and palladium on activated charcoal (10% m:m, 4.3 g, 0.03 eq.) in ethyl acetate (330 mL) and ethanol (235 mL) was flushed with hydrogen, then vigorously stirred for 2 h30 at room temperature. The resulting back suspension was filtered through a dicalite pad. The pad was washed with a mixture of ethyl acetate and ethanol then the liquor was evaporated in vacuo to yield 26.3 g (quant.) of the desired product as off-white oil. MS (m/e): 218.2 (M−H, 100%).

Provenance & Evidence