Water → Pyridine, 2-methyl-5-(1-methylethoxy)-

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Reaction Steps

5-Hydroxy-2-methylpyridine (11.0 g, 100 mmol) was dissolved in N,N′-dimethylformamide (100 mL). The resultant mixture was added with sodium hydride (7.2 g, 150 mmol) and 1-methylethane iodide (12 mL, 121 mmol) under ice-cold conditions, and stirred at room temperature overnight. Subsequently, 1-methylethane iodide (4 mL) was added and the resultant mixture was stirred at 60° C. for 4 hours. The reaction solution was added with water and extracted with diethyl ether. The organic layer was washed with brine, dried using sodium sulfate, and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate), and 5-(1-methylethoxy)-2-methylpyridine (12.7 g, yield 84%) was obtained as a yellow oil.

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