Acetonitrile → 3-Oxo-4-phenylbutanenitrile
Reaction equation
[H-].[Na+].[C:3]1([CH2:9][C:10]([O:12]C)=O)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:14](#[N:16])[CH3:15]>C1COCC1>[O:12]=[C:10]([CH2:9][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[CH2:15][C:14]#[N:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 60% sodium hydride in mineral oil (1.00 g, 25.0 mmol) in THF (40 mL) at reflux is added a solution of methyl phenylacetate (2.50 g, 16.6 mmol) and anhydrous acetonitrile (1.74 mL, 33.3 mmol) in THF (40 mL), dropwise. The mixture is stirred at reflux for 6 h, then cooled to room temperature and stirred an additional 16 h. The reaction is quenched with H2O and is stirred for 10 min, after which the mixture is diluted with ethyl acetate and saturated aqueous NaHCO3 solution. The layers are separated and the aqueous layer is extracted with ethyl acetate. The organic layers are washed with brine and dried (Na2SO4). The solvent is removed in vacuo and the crude material is purified via flash column chromatography using a gradient elution of 0-40% ethyl acetate/heptane to afford the title compound as a yellow oil (690 mg, 26%). LCMS: 160.20 (M+H+).