(Trimethylsilyl)imidazole → HCID 57709215, compound

HRID 546823

Reaction equation

HRID 546823 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])N1C=CN=C1.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([CH3:19])([O:20][Si:2]([CH3:1])([CH3:8])[CH3:9])[CH3:18])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 28925(Trimethylsilyl)imidazoleHCID 516892Sodium BicarbonateHCID 126819202-(4-Bromophenyl)propan-2-ol

Product 1

HCID 57709215HCID 57709215, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-trimethylsilylimidazole (80.6 mL, 0.552 mol) was added to a solution of the crude 2-(4-bromo-phenyl)-propan-2-ol in tetrahydrofuran (500 mL) in a nitrogen atmosphere at room temperature, and the mixture was stirred at the same temperature overnight. The reaction mixture was poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel chromatography (n-hexane:ethyl acetate=40:1) to give the title compound as a colorless oil (125.6 g, 87% in two steps).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-8cd1086b1c9341fca47e010f3347dc7a
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Linked notes

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