Propargyl alcohol → (1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methanol

반응식

[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[CH2:13]([OH:16])[C:14]#[CH:15]>C(O)(C)(C)C.O.O>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][N:1]2[CH:15]=[C:14]([CH2:13][OH:16])[N:3]=[N:2]2)=[CH:6][CH:7]=1

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실험 절차

93 mmol 1-(azidomethyl)-4-methoxybenzene, 110 mmol propargyl alcohol were mixed in 230 ml tert-butyl alcohol/H2O (1:1) solution. 1 mmol CuSO4.5H2O and 10 mmol Ascorbic acid sodium salts dissolved in 2 ml water were added into the solution. The mixture was stirred for 2 days. After evaporation, the mixture was purified by flash column to give 55 mmol (1-(4-methoxybenzyl)-1H-1,2,3-triazole-4-yl) methanol. 1H NMR (CDCl3): 7.42 (1H, s), 7.22 (2H, d, JH-H=8.70), 6.88 (2H, d, JH-H=8.70), 5.43 (2H, s), 4.73 (2H, s), 3.79 (3H, s).