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

HRID 2183517Notes

Reaction equation

HRID 2183517 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CC([Si](C)(C)[O:23][CH2:24][C:25]1[N:26]=[N:27][N:28]([CH3:49])[C:29]=1[CH2:30][O:31][Si:32]([C:45]([CH3:48])([CH3:47])[CH3:46])([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(C)C>CCO>[CH3:48][C:45]([Si:32]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[O:31][CH2:30][C:29]1[N:28]([CH3:49])[N:27]=[N:26][C:25]=1[CH2:24][OH:23])([CH3:46])[CH3:47]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 224731964-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)-1-methyl-1h-1,2,3-triazole

Product 1

HCID 69793338[5-({[(1,1-Dimethylethyl)(diphenyl)silyl]oxy}methyl)-1-methyl-1h-[1,2,3]triazol-4-yl]methanolYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-50745dcc918343f694975f3faa25ff80
Source dataset
uspto-grants-2005_05
Patent number
US06900209B2

Reaction notes

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