Ethyl bromoacetate → ethyl {5-[(2',6'-dimethylbiphenyl-3-yl)methoxy]-1H-indol-1-yl}acetate

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Reaction Steps

5-[(2′,6′-Dimethylbiphenyl-3-yl)methoxy]-1H-indole (0.95 g, 2.90 mmol) was dissolved in a mixed solvent of tetrahydrofuran (30 mL) and N,N-dimethylformamide (4 mL). The solution was ice-cooled, and sodium hydride (60% in oil, 0.12 g, 3.0 mmol) was added, and the mixture was stirred at the same temperature for 20 min. Then, ethyl bromoacetate (0.36 mL, 3.25 mmol) was added to the solution, and the mixture was allowed to warm to room temperature and stirred for 2 days. The reaction solution was diluted with ethyl acetate, washed successively with aqueous citric acid solution, water and brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10-1:5) to give the title compound (1.0 g, yield 83%) as a pale-yellow oil.

Provenance & Evidence