反应详情

{4-[(3,4-diaminophenyl)oxy]phenyl}methanol (3.21 g of crude material) was dissolved in 20 ml THF and 10 ml of formic acid. The reaction was heated in a 100 degree Centigrade oil bath for approximately 22 hours. The reaction was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed 5 times with saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was dissolved in 30 ml of THF and 10 ml of 10% aqueous LiOH and heated at 100 degrees Centigrade for 30 minutes. The reaction was diluted with water and ethyl acetate. The organic layer was washed with brine three times, dried over MgSO4, and concentrated under reduced pressure onto basic alumina. The compound was purified by silica gel column chromatography (100% dichloromethane to 10% (2M NH3 in methanol) in dichloromethane gradient) to give 1.26 g of [4-(1H-benzimidazol-5-yloxy)phenyl]methanol.

1. temperatureThe reaction was heated in a 100 degree Centigrade oil bath for approximately 22 hours
2. concentrationThe reaction was concentrated under reduced pressure
3. dissolutionThe residue was dissolved in ethyl acetate
4. washwashed 5 times with saturated aqueous NaHCO3
5. dry with materialThe organic layer was dried over MgSO4
6. concentrationconcentrated under reduced pressure
7. dissolutionThe residue was dissolved in 30 ml of THF
8. temperature10 ml of 10% aqueous LiOH and heated at 100 degrees Centigrade for 30 minutes
9. additionThe reaction was diluted with water and ethyl acetate
10. washThe organic layer was washed with brine three times
11. dry with materialdried over MgSO4
12. concentrationconcentrated under reduced pressure onto basic alumina
13. customThe compound was purified by silica gel column chromatography (100% dichloromethane to 10% (2M NH3 in methanol) in dichloromethane gradient)