Imidazole → HCID 22244044, compound

HRID 245378Notes

Reaction equation

HRID 245378 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].[F:19][C:20]1[C:25]([F:26])=[C:24]([F:27])[CH:23]=[CH:22][C:21]=1[CH2:28][OH:29].N1C=CN=C1>C(Cl)Cl>[C:1]([Si:5]([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)[O:29][CH2:28][C:21]1[CH:22]=[CH:23][C:24]([F:27])=[C:25]([F:26])[C:20]=1[F:19])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 2777027(2,3,4-Trifluorophenyl)methanol

Product 1

HCID 22244044HCID 22244044, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butylchlorodiphenylsilane (8.86 ml, 34 mmol) was added slowly via syringe to a solution of (2,3,4-trifluorophenyl)methanol (5.0 g, 31 mmol) and imidazole (2.53 g, 37.2 mmol) in CH2Cl2 (30 ml) cooled in an ice water bath. The mixture warmed to room temperature and stir overnight. Solvent was removed and the residue was partitioned between Et2O and water. The Et2O was separated and washed with brine, and the combined aqueous layers were twice more extracted with Et2O, which was washed with brine. Drying (MgSO4) and removal of solvent gave an oil that was chromatographed on silica gel (50% CH2Cl2 in hexanes followed by gradient elution to 100% CH2Cl2) to isolate an oil that slowly solidified to afford 11.9 g (96%) of a white solid.

Workup

  1. temperaturecooled in an ice water bath
  2. customSolvent was removed
  3. customthe residue was partitioned between Et2O and water
  4. customThe Et2O was separated
  5. washwashed with brine
  6. extractionthe combined aqueous layers were twice more extracted with Et2O, which
  7. washwas washed with brine
  8. customDrying
  9. custom(MgSO4) and removal of solvent
  10. customgave an oil that
  11. customwas chromatographed on silica gel (50% CH2Cl2 in hexanes followed by gradient elution to 100% CH2Cl2)
  12. customto isolate an oil that

Sources & evidence

ORD record
ord-b977550751e746f69636b78d3e3e892c
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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