Acetonitrile → 3-Cyclohexyl-3-oxopropanenitrile

Participants

Reaction Conditions

Reaction Steps

To 700 mL of THF cooled at −78° C. under inert atmosphere was added n-butyllithium (56 mL, 2.5 M in hexane) followed by CH3CN (7.3 mL, 0.14 mol) maintaining the temperature below −70° C. The mixture was stirred at −78° C. for 20 min then a solution of methyl cyclohexane carboxylate (10 g, 0.07 mol) in dry THF (300 mL) was added dropwise, maintaining the temperature under −60° C. The reaction was stirred an additional 20 min at −78° C., warmed to −20° C. and quenched by addition of saturated aq. NH4Cl. The reaction mixture was diluted with H2O and extracted with t-BuOMe. The solvents were removed under vacuum to give 3-cyclohexyl-3-oxopropanenitrile as a colorless oil.

Provenance & Evidence