Imidazole → HCID 532661, compound

HRID 1977445Notes

Reaction equation

HRID 1977445 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].N1C=CN=C1.O>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 7638MonobenzoneHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 532661HCID 532661, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Benzyloxyphenol (39 g, 0.19 mole) and tert-butyldimethylsilyl chloride (32.31 g, 0.21 mole) were dissolved in dimethylformamide (200 ml). Imidazole (14.59 g, 0.21 mole) was added in portions and after the addition the reaction mixture was stirred overnight. Water was added and the mixture was extracted with ether. The combined organic layers were washed with water and dried over anhydrous calcium chloride. The solvent was evaporated to yield crystallized product (60.2 g, 0.19 mole, 98%).

Workup

  1. additionafter the addition the reaction mixture
  2. extractionthe mixture was extracted with ether
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over anhydrous calcium chloride
  5. customThe solvent was evaporated
  6. customto yield

Sources & evidence

ORD record
ord-8bf19883f52b497883696206d8ec50f9
Source dataset
uspto-grants-2001_05
Patent number
US06232430B1

Reaction notes

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