Dimethylformamide → 1-(4-Cyanobutyl)cyclopentane carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:10][CH2:11][CH2:12][CH2:13]Br)[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[C-]#N.[Li+].[CH3:18][N:19](C=O)C>>[CH3:1][O:2][C:3]([C:5]1([CH2:10][CH2:11][CH2:12][CH2:13][C:18]#[N:19])[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4]Participants
4
Procedure
A solution of 1-(4-bromobutyl)cyclopentane carboxlic acid methyl ester was treated with a solution of 0.5 molar lithium cyanide in DMF (5 mmol, 10 mL) and stirred overnight at room temperature followed by heating at 75° C. for two hrs. The reaction mixture was evaporated to dryness, the residue was dissolved in ethyl acetate (30 mL) and washed with sat'd sodium bicarbonate (2×10 mL), and brine (5 mL) and dried over magnesium sulfate to give a yellow oil (860 mg). Silica gel chromtography eluting with 1:3 ethyl acetate:hexane yielded a pale oil (83%, 693 mg). LR MS (C12H19NO2): Obs mass, 227 (M+NH4), 248 (M+K).