Imidazole → 1-Benzyloxy-4-diphenyl(tert-butyl)silyloxybenzene

HRID 1634724Notes

Reaction equation

HRID 1634724 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.[C:16]([Si:20](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:19])([CH3:18])[CH3:17].N1C=CN=C1>C(Cl)Cl>[C:16]([Si:20]([O:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 7638MonobenzoneHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 5326061-Benzyloxy-4-diphenyl(tert-butyl)silyloxybenzeneYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-benzyloxyphenol (100 g, 360 mmol), t-butylchlorodiphenylsilane (72.8 g, 360 mmol), and imidazole (24.5 g, 360 mmol) in 1 L of methylene chloride was stirred overnight at ambient temperature. The reaction mixture was washed with water, sat'd NaHCO3 and brine. After drying (Na2SO4), the solvent was evaporated to provide, 155 g of the title compound

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialAfter drying (Na2SO4)
  3. customthe solvent was evaporated
  4. customto provide

Sources & evidence

ORD record
ord-89a97ed8999944119161104946f408fe
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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