Water → Indole-3-propanol

Participants

Reaction Steps

A suspension of lithium aluminum hydride (4.68 g, 126 mmol) in 230 mL anhydrous diethylether was stirred heavily. 3-Indole propionic acid (10.0 g, 53 mmol) dissolved in 460 mL anhydrous diethylether was transferred to a dropping funnel and added at such a rate that gentle reflux was maintained. The reaction mixture was left with stirring at reflux temperature for 2 h, then at room temperature overnight. Then reflux was continued for 2 h before cooling to room temperature. 25 mL H2O was slowly added followed by 70 mL H2O/H2SO4 (1:3 H2O/H2SO4). The resulting clear mixture was extracted with 110 mL diethylether three times. The combined organic phases were washed with brine, dried with Na2SO4, filtrated and concentrated to bright oil, which was used without further purification.

Provenance & Evidence