Imidazole → HCID 57927228, compound

HRID 889146Notes

Reaction equation

HRID 889146 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([F:13])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[C:19]([Si:23]([CH3:26])([CH3:25])Cl)([CH3:22])([CH3:21])[CH3:20].O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:8][CH2:9][C@@H:10]([F:13])[CH2:11][O:12][Si:23]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:26])[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 10773837HCID 10773837, compound

Product 1

HCID 57927228HCID 57927228, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

After dissolving (S)-3-benzyloxy-2-fluoropropan-1-ol (CAS 197389-28-9) (6.00 g) and imidazole (2.44 g) in N,N-dimethylformamide (60 ml), the mixture was cooled on ice. Next, tert-butyldimethylchlorosilane (5.57 g) was added and the mixture was stirred at room temperature for 16 hours. Water was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was washed with water, a saturated aqueous solution of ammonium chloride, water and brine in that order and then dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography. The title compound (9.48 g) was thus obtained.

Workup

  1. temperaturethe mixture was cooled on ice
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of ammonium chloride, water and brine in that order and then dried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1ca58a0325e04f6db274bbc63f06a629
Source dataset
uspto-grants-2012_08
Patent number
US08252810B2

Reaction notes

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