Toluene → 1-[4-(4-methoxyphenyl)butan-1-yl]-1H-1,2,3-triazole

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Reaction Steps

1-(4-Aminobutyl)-4-methoxybenzene hydrochloride (1.0 g, 4.64 mmol) was dissolved in water. Toluene (10 ml) and 2N-sodium hydroxide (10 ml) were added and the mixture was partitioned. The organic layer was washed with 20% brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was dissolved in methanol (8 ml), and a suspension of 2,2-dichloroacetaldehyde tosylhydrazone (2.61 g, 9.28 mmol) in methanol (12 ml) was added dropwise at 15-20° C. The mixture was stirred at room temperature for 2 hours and concentrated under reduced pressure. To the residue was added ethyl acetate (50 ml) and then was added saturated aqueous sodium hydrogen carbonate (50 ml). The mixture was stirred for 10 min and partitioned, which was followed by washing with saturated brine and concentration under reduced pressure. Purification by silica gel column gave 1-[4-(4-methoxyphenyl)butan-1-yl]-1H-1,2,3-triazole (1.1 g, yield 100%).

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