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

HRID 2099144Notes

Reaction equation

HRID 2099144 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3].N1C=CN=C1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>CN(C=O)C>[C:19]([Si:16]([CH3:18])([CH3:17])[O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][CH:6]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

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

Product 1

HCID 10857908Ethanone, 1-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-Yield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxyacetophenone (10.0 g, 73.5 mmol) in DMF (74 mL) was added imidazole (12.0 g, 176.3 mmol) and tert-butyldimethylsilyl chloride (13.3 g, 88.1 mmol). The colorless solution was stirred for 0.75 h at rt then quenched with saturated aqueous NaHCO3. The aqueous phase was extracted with hexanes and the combined organic layers were washed with saturated NaHCO3. The organic layers were dried over sodium sulfate, filtered, and concentrated to provide 1-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-ethanone (18.0 g, 98%) as a white solid which was utilized without further purification. ESI MS (m/z 251, M+H).

Workup

  1. customthen quenched with saturated aqueous NaHCO3
  2. extractionThe aqueous phase was extracted with hexanes
  3. washthe combined organic layers were washed with saturated NaHCO3
  4. dry with materialThe organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bb99a74ce2d0456abfe1ee8ed33bf140
Source dataset
uspto-grants-2009_08
Patent number
US07569568B2

Reaction notes

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