Water → Indole-3-propanol

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of LiAlH4 (4.02 g) in THF (200 mL) at 0° C. and under N atmosphere was added dropwise a THF solution (100 mL) containing indole-3-propanoic acid (20.0 g). After the addition was complete, the reaction was heated at reflux for 16 h, after which time the mixture was cooled to 0° C. and water (4 mL) added, followed by 15% NaOH (4 mL), and finally additional water (12 mL). The reaction was filtered and the THF filtrate extracted with 5% NaOH (4 mL), and finally additional water (12 mL). The reaction was filtered and the THF filtrate extracted with 5% NaHCO3 followed by a sat. NaCl solution. The organic phase was dried with anhydrous K2CO3, filtered, and concentrated under reduced pressure to yield 3-(3-hydroxypropyl)indole (VI; 7.5 g; 41%).

Provenance & Evidence