Imidazole → HCID 59659897, compound

HRID 2238654Notes

Reaction equation

HRID 2238654 reaction equation
[C:1]([Si:5](Cl)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[OH:19][C:20]1[CH:25]=[CH:24][C:23]([C:26](=[O:28])[CH3:27])=[CH:22][CH:21]=1.N1C=CN=C1.CN(C)C=O>C(OCC)(=O)C>[Si:5]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26](=[O:28])[CH3:27])=[CH:22][CH:21]=1)([C:1]([CH3:4])([CH3:3])[CH3:2])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 74694'-HydroxyacetophenoneHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 59659897HCID 59659897, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

11.7 mL of t-butylchlorodiphenyl silane was added to the mixture of 5 g of 1-(4-hydroxyphenyl)-1-ethanone, 3 g of imidazole, and 70 mL of N,N-dimethylformamide, and stirred overnight at room temperature. The reaction mixture was added with 200 mL of ethyl acetate, washed with water and saturated brine in the subsequent order, and the obtained organic layer was dried over anhydrous magnesium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to obtain 11.7 g of 1-(4-{[t-butyl(diphenyl)silyl]oxy}phenyl)-1-ethanone [79-1] as a white solid.

Workup

  1. washwashed with water and saturated brine in the subsequent order
  2. dry with materialthe obtained organic layer was dried over anhydrous magnesium sulfate
  3. filtrationThe insolubles were filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-500a73a50403450fb81a4cc6fcaf3dff
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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