Imidazole → HCID 21185505, compound

HRID 1384056Notes

Reaction equation

HRID 1384056 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-a2ecf23a0e324dc7a1ad98db03eb18cd
Source dataset
uspto-grants-2001_07
Patent number
US06258360B1

Reaction notes

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