Imidazole → HCID 532656, compound

HRID 2167329Notes

Reaction equation

HRID 2167329 reaction equation
N1C=CN=C1.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>C1COCC1.O>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 90154-MethoxyphenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 532656HCID 532656, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Imidazole (1.80 g, 26.1 mmol) and p-methoxyphenol (1.62 g, 13.05 mmol) were suspended in THF (30 mL) and placed under nitrogen. Tert-butyldimethylsilyl chloride (2.23 g, 14.36 mmol) was added and the mixture was stirred for 15 hours at room temperature. The thick white mixture was diluted with water (50 mL) and extracted with ether (3×15 mL). The organic solvent was removed under reduced pressure to give the product as a clear liquid (2.33 g, 75%). Characterization matched literature.

Workup

  1. extractionextracted with ether (3×15 mL)
  2. customThe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cf7ba4b2f5aa40dc9def74c48a2a623d
Source dataset
uspto-grants-2015_06
Patent number
US09045442B2

Reaction notes

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