Imidazole → HCID 23017932, compound

HRID 1616724Notes

Reaction equation

HRID 1616724 reaction equation
N1C=CN=C1.[CH3:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)(=[O:9])=[O:8].[C:17]([Si:21]([CH3:24])([CH3:23])Cl)([CH3:20])([CH3:19])[CH3:18]>CN(C)C=O.[Cl-].[Na+].O>[C:17]([Si:21]([O:16][C:13]1[CH:14]=[CH:15][C:10]([S:7]([CH3:6])(=[O:8])=[O:9])=[CH:11][CH:12]=1)([CH3:24])[CH3:23])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1233504-(Methylsulfonyl)phenol

Product 1

HCID 23017932HCID 23017932, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

9.9 g (145.18 mmol) of imidazole was added to and dissolved in an N,N-dimethylformamide solution (150 mL) of 10 g (58.07 mmol) of 4-methylsulfonylphenol, and then 10.5 g (69.7 mmol) of tert-butyldimethylchlorosilane was added thereto and stirred. After the reaction, brine was added thereto and extracted with ethyl acetate. The organic layer was washed three times with brine, and dried over anhydrous magnesium sulfate. Purifying by silica gel column chromatography (hexane/ethyl acetate=5/1→3/1) gave 15.97 g (55.75 mmol) of tert-butyl-(4-methanesulfonylphenoxy)dimethylsilane (XII-6) (yield 96%). Its physical properties are shown below.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed three times with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customPurifying by silica gel column chromatography (hexane/ethyl acetate=5/1→3/1)

Sources & evidence

ORD record
ord-d981c0048d6c4022bcb249a50669402d
Source dataset
uspto-grants-2014_07
Patent number
US08765814B2

Reaction notes

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