Triethyl phosphonoacetate → Ethyl 3-methyl-5-phenylpent-2-enoate

Participants

Reaction Steps

Ethyl diethylphosphonoacetate (1.67 g, 7.42 mmol) was added dropwise to a solution of potassium tert-butoxide (0.83 g, 7.42 mmol) in tetrahydrofuran (10 ml), followed by stirring at room temperature for 10 minutes. Then, a solution of benzylacetone (1.00 g, 6.75 mmol) in tetrahydrofuran (10 ml) was added drop-wise thereto, and the resulting mixture was stirred at room temperature for 1 hour and then heated under reflux for another 1 hour. The reaction mixture was poured into a 5% aqueous potassium hydrogensulfate solution and extracted with ethyl acetate. The extract solution was washed with water and an aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.82 g of ethyl 5-phenyl-3-methyl-2-pentenoate.

Provenance & Evidence