Methyl 3-phenylpropionate → Dimethyl(2-oxo-4-phenylbutyl)phosphonate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of dimethyl methylphosphonate (8.85 g, 0.071 mol) in 150 ml of anhydrous THF at -78° C. was added dropwise a solution of n-butyl lithium in hexane (1.67N, 43.1 ml, 0.072 mol) under argon atmosphere, and the mixture was stirred for 30 minutes. To this reaction solution was added methyl 3-phenylpropionate (5.0 g, 0.030 mol) in 10 ml of anhydrous THF. After being stirred for 30 minutes, the reaction mixture was allowed to warm to 0° C., diluted with 5.5 ml of acetic acid and 10 ml of water, and concentrated. 30 ml of water was added to the residue and the mixture was extracted with ethyl acetate (100 ml×2). The combined organic layers were washed with water (20 ml) and brine (20 ml), dried over anhydrous sodium sulfate, and concentrated. The residue was distilled under reduced pressure to give a colorless transparent oil of dimethyl 2-oxo-4-phenylbutylphosphonate (7.39 g, 0.029 mol, yield 96%, b.p. 104°-105° C./0.23 mmHg).

Provenance & Evidence