Methyl indole-6-carboxylate → 6-Hydroxymethylindole

Participants

Reaction Steps

To a suspension of lithium aluminium hydride (6.18 g, 2 mol. eq.) in dry THF (350 ml) under nitrogen was added dropwise a solution of methyl indole-6-carboxylate (14.2 g, 81.1 mmol) in dry THF (350 ml) and stirred for 4 hours. The gelatinous suspension was quenched with 2N hydrochloric acid, extracted into diethyl ether, and the combined organic extracts dried, filtered and evaporated in vacuo to yield a yellow oil.

Provenance & Evidence