Phenacyl bromide → Ethyl 2-acetyl-4-oxo-4-phenylbutanoate

Reaction equation

[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15]>O1CCCC1>[C:3]([CH:2]([CH2:13][C:14](=[O:15])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:1]([O:7][CH2:8][CH3:9])=[O:6])(=[O:4])[CH3:5]

Participants

Procedure

To a solution of ethyl acetoacetate (10 g, 76.8 mmol) in tetrahydrofuran (50 ml) at 0° C. was added sodium hydride (4 g, 60% in mineral oil, 100 mmol) portionly. The reaction mixture was stirred for minutes, and 2-bromoacetophenone (16.8 g, 84.5 mmol) in tetrahydrofuran (20 ml) was added dropwisely. After warming the mixture to room temperature, it was stirred for 4 hours. The resulting solution was quenched with water and normal work-up accomplished with diethyl ether. The organic layer was dried with MgSO4, and purified by silica gel column chromatography (EtOAc:Hx=1:5) to produce desired compound (19 g, 98%) as light yellow color oil.