Ethyl Acetate → 1-(4-Methoxybenzyl)-1,2,4-triazole

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Reaction Steps

1,2,4-Triazole (7.5 g, 0.109 mol) was dissolved in dimethylformamide (50 mL) and stirred under a nitrogen atmosphere in an ice bath at 10° C. while partially ground pellets of sodium hydroxide (17.5 g, 0.438 mol) were added in one portion causing an exotherm to about 25° C. A solution of 4-methoxybenzyl chloride (15 mL, 0.111 mol) in DMF was added dropwise over five minutes at 25° C. After stirring at room temperature for four hours, ethyl acetate and water were added. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed four times with water and once with brine and dried over magnesium sulfate. The mixture was filtered and the filtrate solvent evaporated in vacuo to afford the title product as an oil in 69% yield; 14.15 g; 1H NMR (CDCl3) δ 8.00 (s, 1), 7.93 (s, 1), 7.19 (d, 2), 6.88 (d, 2), 5.23 (s, 2), 3.78 (s, 3). mass spectrum: m/z 109 (M+1).

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