Imidazole → (3-Benzyloxy-phenoxy)-tert-butyl-dimethyl-silane

HRID 406003Notes

Reaction equation

HRID 406003 reaction equation
[C:1]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[CH2:14]([O:21][C:22]1[CH:23]=[C:24]([OH:28])[CH:25]=[CH:26][CH:27]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>C1COCC1>[CH2:14]([O:21][C:22]1[CH:23]=[C:24]([CH:25]=[CH:26][CH:27]=1)[O:28][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 138048Benzyl 3-hydroxyphenyl ether

Product 1

HCID 58421755(3-Benzyloxy-phenoxy)-tert-butyl-dimethyl-silane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

43.459 ml tert-butyl-chloro-dimethyl-silane were added at rt to a solution of 17 g imidazole and 25 g 3-benzyloxy-phenol in 400 ml THF. After 3 hours water was added to the reaction mixture and the mixture was then extracted with methylene chloride. The organic phase was extracted three times with water, dried over sodium sulfate and concentrated in vacuo. The residue was solved in methylene chloride and filtered over Alox (neutral) and concentrated.

Workup

  1. extractionthe mixture was then extracted with methylene chloride
  2. extractionThe organic phase was extracted three times with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. filtrationfiltered over Alox (neutral)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6713a2e50caa4e53991e4168637aff95
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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