Dimethylcarbamoyl Chloride → 4-Pentyl-2-cyanopyridine

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Reaction Steps

To trimethylsilyl cyanide (5.2 g, 52 mmol), 4-benzyloxy-pyridine 1-oxide (8.8 g, 44 mmol) in DCM (20 mL) was added, followed by dimethylcarbamoyl chloride (5.6 g, 52 mmol) in DCM (10 mL), dropwise, stirred at room temperature overnight. Sodium bicarbonate (100 mL, 10%) was added, stirred for 10 minutes and extracted twice with DCM (50 mL). The combined organic layer was dried over magnesium sulfate, solvent was removed to obtain the product, compound 10a (R9=Benzyloxy) (10.5 g, 100%).

Provenance & Evidence