3-oxo-5-phenylpentanenitrile

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of cyanoacetic acid (1.0 g, 11.8 mmol) in tetrahydrofuran (20 mL) was cooled to −78° C. and treated with 1.6 M n-butyl lithium in hexanes (14.7 mL, 23.5 mmol). The mixture was warmed to −20° C. over 2 hours, cooled to −78° C. and treated with 3-phenylpropionyl chloride (prepared by refluxing a solution of 3-phenylpropionic acid (1.0 g, 6.7 mmol) in thionyl chloride (4 mL) for 3 hours, evaporating and drying). The mixture was stirred at −78° C. for 1 hour and 20% hydrochloric acid added until the pH=3. The mixture was diluted with diethyl ether, washed with saturated sodium bicarbonate, and the organic layer separated and concentrated. The crude product was purified by flash chromatography on silica gel using 0-50% ethyl acetate/hexanes to provide the title compound. MS (ESI) m/e 191 (M+H+NH3). cooled to −78° C. prepared evaporating drying) 20% hydrochloric acid added until the pH=3 The mixture was diluted with diethyl ether washed with saturated sodium bicarbonate the organic layer separated concentrated The crude product was purified by flash chromatography on silica gel using 0-50% ethyl acetate/hexanes