Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → [5-({[(1,1-Dimethylethyl)(diphenyl)silyl]oxy}methyl)-1-methyl-1h-[1,2,3]triazol-4-yl]methanol

Participants

Reaction Conditions

Reaction Steps

Pyridinium para-toluenesulfonate (0.99 g, 3.94 mmol) was added to a stirred solution of 4-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)-1-methyl-1H-1,2,3-triazole (1.77 g, 3.56 mmol) in EtOH (50 ml) and then heated at 50° C. for 6 h. The reaction mixture was concentrated under reduced pressure, then taken up in EtOAc (100 ml) and washed with H2O (100 ml), 2N NaOH (100 ml) and brine (100 ml). After drying, the solvents were removed 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 hydroxymethyltriazole (1.20 g, 89%). 1H NMR (360 MHz, CDCl3) δ 7.68-7.60 (41H, m), 7.50-7.34 (6H, m), 4.78 (2H, s), 4.46 (2H, s), 4.02 (3H, s), 1.04 (9H, s). m/z (ES+) 382 (M+H+).

Provenance & Evidence