Benzyl Alcohol → benzyl 1H-indole-6-carboxylate

Participants

Reaction Steps

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5 g, 26.1 mmol) was added to a stirred solution of benzyl alcohol (2.47 ml, 23.9 mmol), 1H-indole-6-carboxylic acid (3.5 g, 21.7 mmol) and N,N-dimethylaminopyridine (3.4 g, 28.3 mmol) in dichloromethane (40 ml) at room temperature under a nitrogen atmosphere. After 12 h the reaction mixture was poured into 1M hydrochloric acid (200 ml) and extracted with dichloromethane (2×200 ml). The combined organics were dried (MgSO4) and concentrated to give a brown oil. Flash column chromatography (elution with dichloromethane) gave the subtitle compound (5.4 g).

Provenance & Evidence