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

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.

1. stirringthe resulting mixture was stirred at room temperature for 1 hour
2. temperatureheated
3. temperatureunder reflux for another 1 hour
4. extractionextracted with ethyl acetate
5. washThe extract solution was washed with water
6. dry with materialan aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
7. distillationThe solvent was distilled off under reduced pressure

ORD record

ord-947460b5218b4408b0624c827ed2b12c

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06369110B1