Imidazole → HCID 21185505, compound

HRID 48092Notes

Reaction equation

HRID 48092 reaction equation
N1C=CN=C1.[OH:6][C:7]1[C:8](=[O:13])[C:9](=[O:12])[C:10]=1[CH3:11].[C:14]([Si:18]([CH3:21])([CH3:20])Cl)([CH3:17])([CH3:16])[CH3:15].O>CN(C=O)C>[O:12]([C:9]1[C:8](=[O:13])[C:7](=[O:6])[C:10]=1[CH3:11])[Si:18]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 1861313-Hydroxy-4-methylcyclobut-3-ene-1,2-dione

Product 1

HCID 21185505HCID 21185505, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (11 mmol) is added to a solution of compound 93 (5 mmol) and tert-butyldimethylchlorosilane (5.5 mmol) in 5 mL of DMF cooled by an ice bath. The mixture is allowed to warm to room temperature. After 16 hours, the mixture is poured into water (50 mL) and extracted with ether (3×50 mL), the organic phases are washed with brine (50 mL) and dried over anhydrous MgSO4, and the solvent is evaporated in vacuo. The residue is purified by flash chromatography to give the product as a colorless oil.

Workup

  1. temperaturecooled by an ice bath
  2. extractionextracted with ether (3×50 mL)
  3. washthe organic phases are washed with brine (50 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. customthe solvent is evaporated in vacuo
  6. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-29ee4f8a86e24961ac9839e83b80c096
Source dataset
uspto-grants-2004_03
Patent number
US06702705B1

Reaction notes

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