Pyridine → 4-(Pyridin-3-yl)butanenitrile

Participants

Reaction Steps

To a solution of 0.66 mL (5.11 mmol) 3-pyridine propanol in 5 mL CH2Cl2 at 0° C. was added 0.62 mL (7.67 mmol) pyridine and 0.47 mL (6.14 mmol) methanesulfonyl chloride and the reaction stirred for 4 h. The solution was concentrated under reduced pressure and the crude mesylate dissolved in 10 mL DMF. To this solution was added 902 mg (18.41 mmol) sodium cyanide and the reaction stirred at 60° C. for 3 days. Then the solution was cooled, diluted with H2O (30 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were washed with H2O, dried over MgSO4, and the solvent removed under reduced pressure to give a dark red oil. The crude nitrile was purified by dissolving in EtOAc, washing with H2O, concentrating, and filtering through a silica gel plug (5% MeOH in CH2Cl2) to yield 425 mg (57%) of the nitrile.

Provenance & Evidence