Pyridine → HCID 53992408, compound

Temperature

100 °C

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 separated, 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).

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. customThe organic layer was separated
11. washwashed with water
12. dry with materialdried over anhydrous magnesium sulfate
13. customThe solvent was removed by distillation under reduced pressure
14. customThe resulting oily product was purified by column chromatography (eluant: chloroform/ethanol=10/1)
15. additionDiisopropyl ether was added to the resulting white crystals
16. filtrationthe resulting mixture was filtered

ORD record

ord-fbe0e76192cb4d44a2c2c8784dc9d969

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05872117