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

Participants

Reaction Steps

5-Benzyloxy-1-isopropyl-1H-indole-2-carboxylic acid ethyl ester (47.5 g, 1.0 eq.) and lithium hydroxide (6.56 g, 1.1 eq.) in a mixture of tetrahydofuran (360 mL), water (180 mL) and methanol (120 mL) was refluxed for 2 h then the reaction mixture was concentrated in vacuo. The residue was stirred vigorously in aqueous hydrochloric acid (2N, final pH: 2). The white precipitate was filtered, washed with water then dried in vacuo to yield 41.6 g (96%) of the desired product as white oil. MS (m/e): 308.5 (M−H, 100%).

Provenance & Evidence