Ethyl Acetate → 5,6-dihydro-6-methylene-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline

Participants

Reaction Steps

Methyltriphenylphosphonium bromide (1.29 g) was suspended in anhydrous tetrahydrofuran (10 mL) and a solution of potassium t-butoxide (0.45 g) in tetrahydrofuran (10 mL) was added dropwise at room temperature, followed by stirring for 1 hr at room temperature. Subsequently, 0.50 g of 4,5-dihydro-2-(2-phenylethyl)-6H-imidazo[4,5,1-ij]quinolin-6-one obtained in Example 1 was dissolved in anhydrous tetrahydrofuran (10 mL) and the solution was added dropwise and the mixture was stirred at room temperature for 1 hr. To the reaction solution, a saturated aqueous solution of sodium hydrogencarbonate (50 mL) and ethyl acetate (50 mL) were added and then two layers were separated. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: dichloromethane/ethyl acetate) to yield the titled compound as colorless crystals (0.41 g).

Provenance & Evidence