Imidazole → 3-[(Tert-butyldimethylsilyl)oxy]phenol

HRID 265309Notes

Reaction equation

HRID 265309 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>CN(C=O)C.O>[Si:14]([O:2][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][CH:8]=1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 5054ResorcinolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 114474403-[(Tert-butyldimethylsilyl)oxy]phenolYield 48.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of resorcinol (5.5 g, 50 mmol) in anhydrous DMF (15 mL) was added imidazole (7.14 g, 210 mol %) and tert-butyldimethylsilyl chloride (7.53 g, 105 mol %). The reaction mixture was stirred for 20 h. The reaction mixture was diluted with water (a white precipitate formed) and then it was extracted with ether (3×300 mL). The combined extract was dried (Na2SO4), filtered and concentrated to yield 5.4 g (48.3%) of the title compound; 1H-NMR (CDCl3) δ7.07 (t, 1 H, J=8.0), 6.42 (pseudot, 2 H, J=7.6), 6.36 (s, 1 H), 5.06 (bs, 1 H), 0.98 (s, 9 H), 0.20 (s, 6 H); 13C--NMR (CDCl3) δ157.90, 156.51, 129.89, 112.66, 108.42, 107.53, 25.61, 18.14, 14.49.

Workup

  1. customformed) and then it
  2. extractionwas extracted with ether (3×300 mL)
  3. extractionThe combined extract
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3ffea16a6b2140d3a4ebdcdf246b51fc
Source dataset
uspto-grants-1997_07
Patent number
US05648354

Reaction notes

Loading…