Diethyl Ether → HCID 23020430, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, a 3.0M solution of methylmagnesium bromide in diethyl ether (3.7 ml, 11.1 mmol) was added dropwise over 5 minutes to a 1M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (22 ml, 22 mmol) at −50° C. (dry ice-acetone bath), followed by stirring as it was for 1 hour. Then, a solution of ethyl (E)-3-(2-furyl)-2-(4-pyridyl)-2-propenoate (2.4 g, 9.87 mmol) in tetrahydrofuran (20 ml) was added dropwise thereinto over 5 minutes. The reaction mixture was stirred for 30 minutes while elevating to room temperature, and then the reaction was terminated by adding hydrochloric acid. After diluting with a saturated aqueous ammonium chloride solution, the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography (elution solvent; hexane:ethyl acetate=1:1 to 4:1), to give the title compound (0.52 g, 23%).

Provenance & Evidence