Imidazole → Ethanone, 1-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-

HRID 2269221Notes

Reaction equation

HRID 2269221 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[C:11]([Si:15]([CH3:18])([CH3:17])Cl)([CH3:14])([CH3:13])[CH3:12].N1C=CN=C1>CN(C)C=O>[Si:15]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 74694'-HydroxyacetophenoneHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 10857908Ethanone, 1-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-Yield 56.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-dimethylformamide (70 ml), was mixed with 5.00 g (36.7 mmol), of 4′-hydroxyacetophenone, 6.64 g (44.1 mmol), of tert-butyldimethylchlorosilane, and 6.00 g (88.1 mmol), of imidazole and the mixture was stirred for 12 hours at room temperature. The reaction mixture was poured onto ice water to stop the reaction and extracted with 100 ml of ethyl acetate. The organic extract was washed with 100 ml of water ten times and then with saturated saline and dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (chloroform 100%), to obtain 5.23 g (yield: 56.9%), of the target compound.

Workup

  1. additionThe reaction mixture was poured onto ice water
  2. customthe reaction
  3. extractionextracted with 100 ml of ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with 100 ml of water ten times
  6. dry with materialwith saturated saline and dried with anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (chloroform 100%)
  9. customto obtain 5.23 g (yield: 56.9%)

Sources & evidence

ORD record
ord-46d228973675406db45f32c53b240274
Source dataset
uspto-grants-2001_12
Patent number
US06329399B1

Reaction notes

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