Sodium Chloride → Ethyl 5-methyl-5-phenyl-4-pentenoate

A mixture of potassium tert-butoxide (10.27 g, 91.6 mmol), 3-carboethoxypropyltriphenylphosphonium bromide (41.87 g, 91.6 mmol) and tetrahydrofuran (300 ml) was stirred at room temperature. Acetophenone (10.0 g, 83.2 mmol) was added dropwise to the mixture, and the resulting mixture was stirred at room temperature for another 1 hour and then allowed to stand overnight. Water (100 ml) was added to the reaction mixture, and the resulting mixture was stirred at room temperature for 1 hour, poured into an aqueous sodium chloride solution, and then extracted twice with ethyl acetate. The extract solution was washed with a 5% 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=2/98) to obtain 17.3 g of ethyl 5-methyl-5-phenyl-4-pentenoate.

1. stirringthe resulting mixture was stirred at room temperature for another 1 hour
2. stirringthe resulting mixture was stirred at room temperature for 1 hour
3. extractionextracted twice with ethyl acetate
4. washThe extract solution was washed with a 5% aqueous sodium chloride solution
5. dry with materialdried over anhydrous magnesium sulfate
6. distillationThe solvent was distilled off under reduced pressure
7. customthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/98)

ORD record

ord-28ae1373664042af972861e6710defd4

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06369110B1