Aluminium lithium hydride → HCID 19870607, compound

Participants

Reaction Steps

A suspension of lithium aluminum hydride (1.71 g) in dry tetrahydrofuran (90 ml) was added slowly via cannula to methyl 3-propionylindole-6-carboxylate (1.6 g) as a stirred suspension in dry tetrahydrofuran (60 ml) under an atmosphere of nitrogen. After addition was complete, the mixture was heated to reflux for 90 min, then cooled and poured carefully onto ice (200 ml). The mixture was extracted with ethyl acetate; the extracts were washed (water (twice), brine), dried (MgSO4) and evaporated to give a dark oil. The product was purified by flash chromatography, eluting with 7:3 hexane:ethyl acetate, to give 6-hydroxymethyl-3-propylindole (1.2 g, 92%) as a white solid; mp 68°-71°; partial NMR (250 MHz, DMSO-d6): 0.93(t, 3H, CH2CH3), 1.64(m, 2H, CH2CH3), 2.65(t, 2H, CH2CH2CH3), 4.55(d, 2H, CH2OH), 5.03(t, 1H, OH), 10.67(br s, 1H, NH).

Provenance & Evidence