Sodium hydride → HCID 68420703, compound

Participants

Reaction Steps

To a suspension of trimethylsulfoxonium iodide (2.88 g, 13.1 mmol) in dimethyl sulfoxide (10 mL) was added 60% sodium hydride (150 mg, 11.2 mmol), and the mixture was stirred at room temperature for 2.5 hr. To the reaction mixture was added methyl 3-[(1E)-2-cyanoethenyl]benzoate (700 mg, 3.74 mmol), and the mixture was stirred at room temperature for 16 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution (30 mL), and the mixture was extracted with ethyl acetate (30 mL, 10 mL). The combined organic layer was washed with saturated brine (5 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5→85/15), and the fractions containing the object product were concentrated under reduced pressure to give the title compound (205 mg, 27%) as a colorless solid.

Provenance & Evidence