Diisopropylamine → 3-(1-Methylcyclopropyl)-3-oxopropanenitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (7.43 ml, 52.6 mmol) in 60 mL of THF at −78° C. was added a solution of n-BuLi in hexanes (2.5M, 21.0 mL, 52.6 mmol). The mixture was stirred at −78° C. for 30 min then acetononitrile (2.76 ml, 52.6 mmol) was added. After 30 min, methyl 1-methylcyclopropanecarboxylate (3.0 g, 52.6 mmol) was added and the reaction mixture was stirred at −78° C. for 1 hour then allowed to warm to room temperature and stirred overnight. The mixture was concentrated and the residue was diluted with water and extracted with ether. The aqueous phase was acidified with 6N aqueous HCl to pH 2-3 and extracted with ether. The combined organic extracts were dried over MgSO4, filtered, and concentrated to afford the title compound 2.89 g (89%). MS (DCI/NH3) m/z 124 (M+H)+.

Provenance & Evidence