Benzyl Alcohol → HCID 67000056, compound

Participants

Reaction Steps

3-(3-Azidocarbonyl-propyl)-5-bromo-1H-indole-2-carboxylic acid ethyl ester (1.28 g, 3.4 mmol, 1.0 equiv), TsOH hydrate (65 mg, 0.34 mmol, 0.1 equiv), and benzyl alcohol (0.74 mL, 6.8 mmol, 2.0 equiv) were refluxed in 30 mL of benzene for 16 h. The solution was then poured into saturated aqueous sodium bicarbonate (50 mL) and extracted with 2×50 mL of diethyl ether. The pooled organic fractions were dried (Na2SO4), filtered, and evaporated. The residue was purified by flash chromatography on silica gel using 0% EtOAc in hexanes graded to 20% EtOAc in hexanes to provide 5-bromo-3-[3-benzyloxycarbonyl-propyl]-1H-indole-2-carboxylic acid ethyl ester (1.3 g, 75%). This material was used without further manipulation.

Provenance & Evidence