[OH:1][C:2]([CH:4]=[CH2:5])=[O:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=O)[CH3:26].CCOCC.O>CS(C)=O.O1CCCC1>[C:28]1([C:25]([CH3:26])=[CH:5][CH2:4][C:2]([OH:1])=[O:3])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1
Sodium hydride (1.70 g., 57% in oil dispersion) is washed free of oil using hexane under nitrogen, and then 7.4 g (20 mmole) of triphenylphosphine hydroxycarbonylethylene and 2.4 g (20 mmole) of acetophenone in 25 ml of dimethylsulfoxide (DMSO) and 20 ml of tetrahydrofuran (THF) are added. The reaction is stirred overnight at RT and then poured into ether and water. The aqueous phase is washed (2X) with ether and then acidified with 2 N sulfuric acid followed by extraction into ether. The organic phase is washed with water, dried over calcium sulfate and solvent removed to give 4-phenyl-3-pentenoic acid.
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