Hydrochloric Acid → HCID 67332216, compound

Participants

Reaction Steps

Benzyltriphenylphosphonium chloride (29.67 g, 76.30 mmol) was added to a solution of potassium tertbutoxide (9.34 g, 83.24 mmol) in tetrahydrofuran (300 ml), followed by stirring at room temperature for 3 hours, and ethyl levulinate (10.00 g, 69.36 mmol) was added dropwise thereto. The reaction mixture was stirred at room temperature for 2 hours and then heated under reflux for another 2 hours. The reaction mixture was adjusted to pH 1 with a 1N-aqueous hydrochloric acid solution and extracted with ethyl acetate, and the extract solution was washed with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/25) to obtain 9.20 g of ethyl 4-methyl-5-phenyl-4-pentenoate.

Provenance & Evidence