Imidazole → HCID 68525592, compound

HRID 884098Notes

Reaction equation

HRID 884098 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][OH:20])=[CH:13][CH:12]=2)=[N:8][CH:9]=1)([O-:3])=[O:2].N1C=CN=C1.[C:26]([Si:30](Cl)([CH3:32])[CH3:31])([CH3:29])([CH3:28])[CH3:27].O>CN(C=O)C>[Si:30]([O:20][CH2:19][CH2:18][CH2:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=2)=[CH:12][CH:13]=1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 68527299HCID 68527299, compound

Product 1

HCID 68525592HCID 68525592, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[4-(5-nitropyridin-2-yloxy)phenyl]-n-propanol (1.17 g, 4.3 mmol) in DMF (10 mL) were added imidazole (580 mg, 8.5 mmol) and t-butylchlorodimethylsilane (640 mg, 4.2 mmol), and the resulting solution was stirred for 13 hours at room temperature. Water was added to the reaction mixture, and extracted with diethyl ether, and the diethyl ether layer was washed with water and then brine. The diethyl ether layer was dried over anhydrous magnesium sulfate, evaporated, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1), to thereby yield 1.14 g of the title compound.

Workup

  1. extractionextracted with diethyl ether
  2. washthe diethyl ether layer was washed with water
  3. dry with materialThe diethyl ether layer was dried over anhydrous magnesium sulfate
  4. customevaporated
  5. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-24d771f607d548a19ea224107a0d499f
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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