Hexane → Benzyl 3-(1-hydroxyethyl)-1H-indole-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Lithium aluminum hydrode (1.2 g, 32 mmol) was suspended in tetrahydrofuran (100 ml) and cooled to -78° C. N-Carbobenzoxy-3-acetyl indole (19.3 g, 66 mmol) dissolved in tetrahydrofuran (200 ml) was added over 0.5 hr. and the reaction mixture was allowed to stir at -78° C. for 0.5 hr and then at 0° C. for 0.5 hr. Ether (300 ml) was added and the mixture was quenched with 1.2 ml H2O, 1.2 ml 2N NaOH, adn 3.6 ml and H2O. The mixture was filtered through celite, dried over MgSO4 and evaporated leaving a solid. The solid was dissolved in 50 ml hot ether and then hexane was added (300 ml). The resulting crystals were collected to afford 12.5 g (64% yield): mp 79°-80° C., which was identical with the material prepared above in procedure A.

Provenance & Evidence