Imidazole → 2-(1H-imidazol-1-yl)-1-phenylethanol

HRID 368353Notes

Reaction equation

HRID 368353 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[CH2:6]1[O:14][CH:7]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CCO.N1C=CC=CC=1>[N:1]1([CH2:6][CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[OH:14])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 795ImidazoleHCID 7276Styrene Oxide

Product 1

HCID 322392-(1H-imidazol-1-yl)-1-phenylethanolYield 35.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 702EthanolSolvent

Procedure

A solution of 17.6 g (0.258 mol) of imidazole in 100 mL of absolute EtOH was treated with 0.6 mL (4.0 mmol) of pyridine and refluxed for 25 minutes. This was then treated dropwise with a solution of 31.06 g (0.258 mol) of styrene oxide and the solution heated at reflux overnight. The solvent was removed under reduced pressure and the residue taken up in Et2O and washed with H2O. A solid separated which was collected and dissolved in warm CHCl3 /EtOAc. The organic phase was washed with saturated NaCl and dried over MgSO4. Treatment of the filtrate with charcoal, filtering, and concentrating to 1/3 volume caused a solid to separate. There was collected 17.09 g (35% yield) of the product as a white solid, mp 146-148° C. The structure was confirmed by NMR and mass spectroscopy. MS m/z 189 (M+H+).

Workup

  1. temperaturerefluxed for 25 minutes
  2. temperaturethe solution heated
  3. temperatureat reflux overnight
  4. customThe solvent was removed under reduced pressure
  5. washwashed with H2O
  6. customA solid separated which
  7. customwas collected
  8. dissolutiondissolved in warm CHCl3 /EtOAc
  9. washThe organic phase was washed with saturated NaCl
  10. dry with materialdried over MgSO4
  11. filtrationTreatment of the filtrate with charcoal, filtering
  12. concentrationconcentrating to 1/3 volume
  13. customto separate

Sources & evidence

ORD record
ord-8336d8604b2f40ef9996e218375cc372
Source dataset
uspto-grants-2000_10
Patent number
US06133303

Reaction notes

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