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

Temperature

50 °C

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+).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. washwashed with H2O (100 ml), 2N NaOH (100 ml) and brine (100 ml)
3. customAfter drying
4. customthe solvents were removed under reduced pressure
5. customthe mixture was purified by column chromatography on silica using 10-100% Et2O/iso-hexanes as eluent

ORD record

ord-50745dcc918343f694975f3faa25ff80

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06900209B2