Methanol → HCID 12799944, compound

Participants

Reaction Conditions

Reaction Steps

A solution of borane in tetrahydrofuran (134 ml, of strength 1M) in portions (13×10 ml) was added during 20 minutes to a stirred solution of methyl 3-(n-dodecanoyl)indole-6-carboxylate (19.9 g) in a mixture of dry tetrahydrofuran (330 ml) and dry ethyl acetate (330 ml), the temperature of the reaction being maintained at 50° C. by external warming. The mixture was stirred and refluxed for 1.5 hours and then methanol (330 ml) was added to the refluxing mixture during 10 minutes. The mixture was refluxed for a further 30 minutes and water (50 ml) was added. The mixture was distilled at atmospheric pressure to remove the organic solvents to give a yellow residue. The residue was triturated with water (50 ml) to give a solid, which was collected and washed with water (100 ml). The solid was recrystallised from methanol (100 ml) (with treatment with charcoal) and then from toluene to give methyl 3-(n-dodecyl)-indole-6-carboxylate (10 g), in the form of a white solid, m.p. 85°-89° C.

Provenance & Evidence