Methyl iodide → 3-(1-Cyanoethyl)pyridine-2-carbonitrile

Beteiligte Stoffe

Reaktionsschritte

To a solution of 3-(cyanomethyl)pyridine-2-carbonitrile (synthesized by the method of Synthesis 1973, 47, 530 mg, 3.70 mmol) in tetrahydrofuran (14 mL) was added dropwise a solution of 1.65 mol/L n-butyllithium in hexane (2.60 mL, 4.29 mmol) at −78° C. under argon atmosphere. The mixture was stirred at the same temperature for 30 minutes, and then thereto was added dropwise iodomethane (300 μL, 4.81 mmol) in tetrahydrofuran (7 mL). The mixture was stirred at the same temperature for 1 hour. The reaction solution was slowly warmed to room temperature, and then to the reaction solution was added water, and the mixture was extracted with ethyl acetate four times. The organic layer was combined, washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→50:50) to give 3-(1-cyanoethyl)pyridine-2-carbonitrile (514 mg, 88%) as a yellow oil.

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