Citric Acid → (1H-indol-2-yl)methanol

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Reaction Steps

To a mixture of indole-2-carboxylic acid (2.0 g, 12 mmol), N,N-dimethylformamide (10 mL), tetrahydrofuran (20 mL) and N-hydroxysuccinimide (1.5 g, 13 mmol) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.9 g, 15 mmol), and the mixture was stirred overnight at room temperature. 0.5 M Aqueous citric acid solution was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated. Tetrahydrofuran (20 mL) and sodium tetrahydroborate (1.9 g, 50 mmol) were added to the residue under ice-cooling, and the mixture was stirred at room temperature for 6 hrs. 0.5 M Aqueous citric acid solution was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5:1) to give the title compound. yield 56%.

Provenance & Evidence