Phenylacetyl chloride → 3-Oxo-4-phenylbutanenitrile

Reaction equation

[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].[Li]CCCC.[C:12]1([CH2:18]C(Cl)=O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[O:6]=[C:4]([CH2:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][C:1]#[N:2]

Participants

Procedure

To a solution of cyanoacetic acid (2 g, 23.5 mmol) in THF (100 mL) at −78° C. was added nBuLi (10 mL, 25.9 mmol, 2.5M in hexanes). After 30 min, phenylacetyl chloride (1.6 mL, 11.8 mmol) was added dropwise. Following an additional 30 min, the solution was partitioned between 1N HCl-Et2O and the aqueous phase was washed several times with Et2O. The combined organic fractions were dried over Na2SO4, concentrated and purified via column chromatography (silica, 30% EtOAc in hexanes) yielding the title compound (770 mg, 40%) as a tan oil: LCMS (ES) m/z 160 (M+H)+.