Borane;tetrahydrofuran → HCID 22627226, compound

Participants

Reaction Steps

To a solution of 3-acetyl-1H-indole-6-carboxylic acid methyl ester (0.65 g, 3.0 mmole) in THF (30 mL) was added BH3-THF (1.0M, 9 mL, 9 mmol). The solution was heated to reflux and then more BH3-THF (5 mL) was added. After allowing to cool and stirring for 2 hr at room temperature, the solvent was removed and the remaining material was diluted in ethyl acetate (100 mL) and washed with dilute NaHCO3 (200 mL). The organic layer was dried (MgSO4), filtered and concentrated. The remaining material was subjected to flash chromatography (25% ethyl acetate/hexanes) to collect 0.45 g (74% yield) of 3-ethyl-1H-indole-6-carboxylic acid methyl ester.

Provenance & Evidence