Imidazole → HCID 70654046, compound

HRID 1429345Notes

Reaction equation

HRID 1429345 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([N+:30]([O-:32])=[O:31])=[C:19]([CH:21]([OH:29])[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:20]=1.O>CN(C)C=O>[Si:6]([O:29][CH:21]([C:19]1[CH:20]=[C:15]([Cl:14])[CH:16]=[CH:17][C:18]=1[N+:30]([O-:32])=[O:31])[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 69915440HCID 69915440, compound

Product 1

HCID 70654046HCID 70654046, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (5.4 g) and tert-butyldimethylsilyl chloride (3.98 g) were added to a solution of ethyl 4-(5-chloro-2-nitrophenyl)-4-hydroxybutanoate (3.8 g) in anhydrous dimethylformamide (25 mL), and stirred at room temperature for 16 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water three times and dried over anhydrous magnesium sulfate. Subsequently, the solvent was distilled off and the residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=20:1→10:1) to obtain 5.3 g of ethyl 4-(tert-butyldimethylsilyloxy)-4-(5-chloro-2-nitrophenyl)butanoate with a quantitive yield.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed with water three times
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationSubsequently, the solvent was distilled off
  5. customthe residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=20:1→10:1)

Sources & evidence

ORD record
ord-9dc3b98deaab485d9a926d3b4ff616cc
Source dataset
uspto-grants-2015_01
Patent number
US08940727B2

Reaction notes

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