O.Cl.[OH:3][CH2:4][C:5]1[N:6]=[N:7][N:8]([CH3:10])[CH:9]=1.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].CCN(CC)CC>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Si:11]([O:3][CH2:4][C:5]1[N:6]=[N:7][N:8]([CH3:10])[CH:9]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]A mixture of 4-hydroxymethyl-1-methyl-1H-[1,2,3]triazole hydrochloride hydrate (WO-A-9850385) (7.0 g, 41.8 mmol), tert-butyldimethylsilyl chloride (6.3 g, 41.8 mmol), Et3N (11.6 ml, 83.6 mmol) and 4-(dimethylamino)pyridine (255 mg, 5 mol %) in CH2Cl2 (250 ml) was stirred at room temperature overnight under N2. Iso-hexanes (400 ml) were added and the resulting precipitate was removed by filtration. The filtrate was concentrated under reduced pressure and the mixture was purified by column chromatography on silica using 10-100% Et2O/iso-hexanes as eluent to yield the desired protected alcohol (8.90 g, 94%). 1H NMR (360 MHz, CDCl3) δ 7.35 (1H, s), 4.73 (2H, s), 3.98 (3H, s), 0.81(9H, s), 0.00 (6H, s).
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