Iodoethane → HCID 66772785, compound

Participants

Reaction Steps

A mixture of 4-benzyloxy-1H-indole-2-carboxylic acid ethyl ester (1.0 g, 3.40 mmol) in DMF (2 mL) was added drop wise to a suspension of NaH (100 mg, 4.0 mmol) in DMF (5 mL). The reaction mixture was stirred for 30 min. Ethyl iodide (624 mg, 4.0 mmol) diluted in 1 mL of DMF was added drop wise at room temperature and the mixture was stirred for an additional 1 hr. The reaction mixture was diluted with 100 mL of EtOAc and washed with 100 mL of saturated ammonium chloride, brine (50 mL), dried over anhydrous sodium sulfate and the solvent was removed to afford crude 4-benzyloxy-1-ethyl-1H-indole-2-carboxylic acid ethyl ester (1.15 g). This material was diluted in 30 mL of ethanol and 100 mg of 10% Pd/C was added. The mixture was placed on a Parr shaker for hydrogenation at 50 psi for 3 hr. The mixture was filtered and the solvent was removed to afford 1-ethyl-4-hydroxy-1H-indole-2-carboxylic acid ethyl ester (0.730 g, 92% yield) as a white solid. LCMS for C13H15NO3 calcd. (m/e) 233, observed 234 (M+H).

Provenance & Evidence