Imidazole → HCID 54422404, compound

HRID 547131Notes

Reaction equation

HRID 547131 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[C:14]([O:25][CH2:26]C)(=[O:24])[C:15]1[CH:23]=[CH:22][C:20]([OH:21])=[C:17]([O:18][CH3:19])[CH:16]=1>CN(C)C=O>[CH3:26][O:25][C:14](=[O:24])[C:15]1[CH:23]=[CH:22][C:20]([O:21][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7])=[C:17]([O:18][CH3:19])[CH:16]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 12038Ethyl vanillateHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 54422404HCID 54422404, compoundYield 104.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (3.47 g, 51.0 mmol) and t-butyldimethylsilyl chloride (3.84 g, 25.5 mmol) were added to a solution of ethyl vanillate (5.0 g, 25.5 mmol) in N,N-dimethylformamide (50 mL) at room temperature, and the mixture was stirred at room temperature for three hours. The reaction solution was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane only to hexane:ethyl acetate=10:1) to give the title compound (7.90 g, 100%).

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (hexane only to hexane

Sources & evidence

ORD record
ord-a42cd8f1c0b04579b46946dc79ad3ab7
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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