Pyridine → HCID 53992408, compound

HRID 862510Notes

Reaction equation

HRID 862510 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][O:7][CH2:8][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[OH:10])[N:3]=[CH:2]1.N1C=CC=C[CH:18]=1.C(OC(=O)C)(=O)C.[OH-].[Na+]>O.C(Cl)(Cl)Cl.C(O)C.C(N(CC)CC)C>[CH3:18][N:3]1[C:4]([CH2:6][O:7][CH2:8][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[OH:10])=[CH:5][N:1]=[CH:2]1

Participants

9

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 178521431HCID 178521431, compound

Product 1

HCID 53992408HCID 53992408, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 500 mg of 2-[(imidazol-4-yl)methoxy]-1-phenylethanol, 1.1 ml of pyridine, 1.1 ml of triethylamine and 1.1 ml of acetic anhydride was stirred for 1 hour at 100° C. The reaction mixture was cooled to room temperature. The solvent was removed by distillation under reduced pressure. To the residue were added 1.1 ml of methyl iodide and 5 ml of acetonitrile. The mixture was allowed to stand at room temperature for 24 hours. The solvent was removed by distillation under reduced pressure. To the residue thus obtained were added 4 ml of ethanol and 6.8 ml of a 5% aqueous sodium hydroxide solution. The resulting mixture was stirred at room temperature for 6 hour. The solvent was removed by distillation under reduced pressure. To the residue thus obtained were added 30 ml of chloroform and 20 ml of water. The organic layer was separatd, washed with water, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The resulting oily product was purified by column chromatography (eluant: chloroform/ethanol=10/1). Diisopropyl ether was added to the resulting white crystals, and the resulting mixture was filtered to obtain 450 mg of 2-[(1-methylimidazol-5-yl)methoxy]-1-phenylethanol (compound No. 214).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe solvent was removed by distillation under reduced pressure
  3. additionTo the residue were added 1.1 ml of methyl iodide and 5 ml of acetonitrile
  4. waitto stand at room temperature for 24 hours
  5. customThe solvent was removed by distillation under reduced pressure
  6. customTo the residue thus obtained
  7. stirringThe resulting mixture was stirred at room temperature for 6 hour
  8. customThe solvent was removed by distillation under reduced pressure
  9. customTo the residue thus obtained
  10. washwashed with water
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was removed by distillation under reduced pressure
  13. customThe resulting oily product was purified by column chromatography (eluant: chloroform/ethanol=10/1)
  14. additionDiisopropyl ether was added to the resulting white crystals
  15. filtrationthe resulting mixture was filtered

Sources & evidence

ORD record
ord-43f3869d64da48029932e1b282bb7f41
Source dataset
uspto-grants-1998_02
Patent number
US05719150

Reaction notes

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