Imidazole → HCID 13007323, compound

HRID 990606Notes

Reaction equation

HRID 990606 reaction equation
CN(C)C=O.[OH:6][C:7]1[CH:8]=[C:9]([CH:18]=[CH:19][CH:20]=1)[C:10]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[O:11].[C:21]([Si:25](Cl)([CH3:27])[CH3:26])([CH3:24])([CH3:23])[CH3:22].N1C=CN=C1>O>[O:6]([C:7]1[CH:8]=[C:9]([CH:18]=[CH:19][CH:20]=1)[C:10]([O:12][CH2:13][C:14]([F:15])([F:16])[F:17])=[O:11])[Si:25]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 130073222,2,2-Trifluoroethyl 3-hydroxybenzoate

Product 1

HCID 13007323HCID 13007323, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 250 mL round bottom flask was added 30 mL of dry dimethyl formamide and 4.0 parts of ester (47) and 3.5 parts of tert-butyldimethyl silyl chloride were added to the reaction flask with stirring. Three parts of Imidazole was added in portions and stirring was continued for 10 hours. The reaction mixture was diluted with 80 mL of water and the product was extracted with ethyl acetate. The organic layer was washed with water and dried on anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give an oil, yield 5.65 parts. The structure was confirmed on the basis of 1H NMR. The reaction proceeded as follows:

Workup

  1. additionwere added to the reaction flask
  2. stirringstirring
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried on anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customto give an oil
  8. customyield 5.65 parts

Sources & evidence

ORD record
ord-4729ed42625648a6a0ca9f5092872787
Source dataset
uspto-grants-2002_10
Patent number
US06461876B1

Reaction notes

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