Synthesis
General procedure: Azidobenzene (1 eq.), 2-propyn-1-ol (1.5 eq.) and copper sulfate pentahydrate (0.1 eq.) were dissolved in a solvent mixture of water and acetonitrile (12 mL, water:acetonitrile = 2:1, v/v) at room temperature. Hydrazine hydrate (1 eq.) was added dropwise to the above solution under vigorous stirring. The reaction mixture gradually changed to light yellow or light green color. The progress of the reaction is monitored by thin layer chromatography (TLC) and the reaction is usually completed within a few minutes (see Table 3 for specific times). Upon completion of the reaction, the product usually precipitates as a colorless solid (unless otherwise noted). The reaction mixture is diluted with excess water and subsequently filtered. The collected solid product is washed with water and dried. The resulting solid may be crystallized by dissolution in a suitable solvent or filtered through a pad of diatomaceous earth to obtain analytically pure 1-phenyl-1hydro-4-methanolyl-1,2,3-triazole.
References
[1] New Journal of Chemistry, 2006, vol. 30, # 8, p. 1137 - 1139
[2] Green Chemistry, 2012, vol. 14, # 5, p. 1298 - 1301
[3] Applied Catalysis A: General, 2013, vol. 453, p. 151 - 158
[4] Archiv der Pharmazie, 2015, vol. 348, # 11, p. 796 - 807
[5] New Journal of Chemistry, 2015, vol. 39, # 8, p. 5902 - 5907
