Water → methyl [2-[1-(((2R)-oxiranyl)methoxy)ethyl]phenyl]propynoate

Participants

Reaction Conditions

Reaction Steps

(R)-2-[[1-(2-Iodophenyl)ethoxy]methyl]oxirane (1.50 g) obtained in Step 1 was dissolved in tetrahydrofuran (15 ml), methyl propynoate (1.66 g), tetrakis(triphenylphosphine)palladium(0) (69.2 mg), copper iodide (37.5 mg) and potassium carbonate (2.72 g) were successively added, and the mixture was stirred overnight at 65° C. The reaction mixture was cooled to room temperature, water was added and, after filtration through celite, the filtrate was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (43 mg).

Provenance & Evidence