[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1.[NH:14]1[CH:18]=[CH:17][N:16]=[N:15]1.[I-].[K+].[Cl-].[Li+].C(O[Na])(C)(C)C>O.C1(C)C=CC=CC=1.C(O)(C)(C)C>[ClH:1].[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:14]2[CH:18]=[CH:17][N:16]=[N:15]2)=[CH:7][CH:8]=11-(4-Chlorobutyl)-4-methoxybenzene (993 mg, 5 mmol), 1H-1,2,3-triazole (691 mg, 10 mmol), potassium iodide (830 mg, 5 mmol) and lithium chloride (424 mg, 10 mmol) were added to t-butanol (5 ml), and t-butoxysodium (961 mg, 10 mmol) was added. The mixture was refluxed under heating for 17 hours. After cooling to room temperature, toluene and water were added and the mixture was partitioned. The organic layer was washed with water, 20% citric acid (three times), saturated aqueous sodium hydrogen carbonate and water, and concentrated under reduced pressure. To the residue was added ethanol (30 ml). Concentrated hydrochloric acid (2 ml) was added and the mixture was concentrated under reduced pressure. To the residue was added 2-propanol, and after concentration under reduced pressure, ethyl acetate was added. The mixture was concentrated under reduced pressure and ethyl acetate (3 ml) was added. The mixture was stirred at room temperature for 45 min. The precipitated crystals were collected by filtration and dried under reduced pressure to give 1-[4-(4-methoxyphenyl)butan-1-yl]-1H-1,2,3-triazole hydrochloride (772 mg, yield 58%).
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