Acetonitrile → 3-Oxo-3-(1-(trifluoromethyl)cyclopropyl)propanenitrile

Participants

Reaction Conditions

Reaction Steps

Add 2 M LDA solution in THF (19.15 mL, 38.3 mmol) to a dry ice-acetone cooled solution of 1-trifluoromethyl-cyclopropane-1-carboxylic acid methyl ester (2.93 g, 17.4 mmol) and acetonitrile (1.43 g mL, 34.8 mmol) in THF (30 mL). Stir reaction mixture at −70° C. for 1.5 hours and then allow to warm to 22° C. for 2 hours. Concentrate, add hexanes, and filter to give a yellow solid. Wash with hexanes and treat with diethyl ether (250 mL) then 2 N HCl (150 mL). Extract aq. layer with diethyl ether (4×100 mL). Dry the combined organic phases over sodium sulfate. Removal of solvent provides 3-Oxo-3-(1-trifluoromethyl-cyclopropyl)-propionitrile (2.99 g, 97% yield). MS (ES−): m/z=176.1 [M+H].

Provenance & Evidence