Indole-3-Acetic Acid → Tryptophol

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of LiAlH4 (3.24 g) in THF (200 mL) at 0° C. and under N2 atmosphere was added dropwise a THF solution (50 mL) containing indole-3-acetic acid (10.0 g). After the addition was complete, the reaction was heated at reflux for 3 h, after which time the mixture was cooled to 0° C. and water (3.3 mL) added, followed by 15% NaOH (3.3 mL), and finally additional water (9.9 mL). The reaction was filtered and the filter cake washed with Et2O. The organic layers were combined, dried with anhydrous MgSO4, filtered, and concentrated under reduced pressure to yield 3-(2-hydroxyethyl)indole (VI; 7.4 g; 80%).

Provenance & Evidence