Imidazole → HCID 59342609, compound

HRID 416168Notes

Reaction equation

HRID 416168 reaction equation
[Cl:1][C:2]1[C:3]([CH3:18])=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=[O:17])[CH:11]=2)[C:5]([CH3:9])=[CH:6][C:7]=1[OH:8].N1C=CN=C1.[C:24]([Si:28]([CH3:31])([CH3:30])Cl)([CH3:27])([CH3:26])[CH3:25].O>CN(C)C=O>[Si:28]([O:8][C:7]1[CH:6]=[C:5]([CH3:9])[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=[O:17])[CH:11]=2)=[C:3]([CH3:18])[C:2]=1[Cl:1])([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 593425823'-Chloro-4'-hydroxy-2',6'-dimethylbiphenyl-3-carbaldehyde

Product 1

HCID 59342609HCID 59342609, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3′-chloro-4′-hydroxy-2′,6′-dimethylbiphenyl-3-carbaldehyde (1.41 g, 5.41 mmol) and imidazole (1.10 g, 16.2 mmol) in N,N-dimethylformamide (10 mL), was added tert-butyldimethylchlorosilane (1.22 g, 8.09 mmol) at room temperature, and the mixture was stirred at room temperature for 24 hr under nitrogen atmosphere. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-20:80) to give the title compound (1.78 g, yield 88%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-20:80)

Sources & evidence

ORD record
ord-c53216fc6bf24b99be8d9ddb222f7bd2
Source dataset
uspto-grants-2012_01
Patent number
US08088821B2

Reaction notes

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