Imidazole → HCID 57704613, compound

HRID 2406053Notes

Reaction equation

HRID 2406053 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[C:6]([CH:9]=1)[CH2:7][OH:8].N1C=CN=C1.[C:24]([Si:28]([CH3:31])([CH3:30])Cl)([CH3:27])([CH3:26])[CH3:25].C(=O)([O-])O.[Na+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[C:6]([CH:9]=1)[CH2:7][O:8][Si:28]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium BicarbonateHCID 3459846HCID 3459846, compound

Product 1

HCID 57704613HCID 57704613, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 35-2 (7.95 g) and imidazole (4.19 g) in N,N-dimethylformamide (35 ml) was added t-butyldimethylchlorosilane (4.45 g) under ice-cooling, and the mixture was stirred for 20 min under ice-cooling, and further at room temperature for 18 hr. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (11.1 g) as a pale-brown oil.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. waitfurther at room temperature for 18 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b1224f6740c8455081da12614aaedae8
Source dataset
uspto-grants-2014_08
Patent number
US08809304B2

Reaction notes

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