Potassium Carbonate → HCID 66778746, compound

Participants

Reaction Steps

To a solution (10 mL) of 1-[2-hydroxy-5-(2-methoxyethoxy)phenyl]ethanone (0.55 g) synthesized in Example A79(1) in N,N-dimethylformamide were added potassium carbonate (1.1 g) and 1-bromo-3-methylbutan-2-one (0.56 g) synthesized in Example A75(1) at room temperature, and the mixture was stirred for 15 hr. The reaction mixture was filtered through celite, water (200 mL) was added and the mixture was extracted with diethyl ether (10 mL×2). The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (10 mL), and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.41 mL) was added to the solution at room temperature. The reaction mixture was stirred at 100° C. for 1 hr. The reaction mixture was allowed to cool to room temperature, 1N hydrochloric acid (10 mL) was added, and the mixture was extracted with diethyl ether (10 mL×2). The extract was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1, volume ratio) to give the title object compound (0.71 g, 98%) as a pale-yellow oil.

Provenance & Evidence