反应详情

To an ice-cooled suspension of methyl 4-((3-benzoylphenoxy)methyl)benzoate (1.62 g, 4.88 mmol) in methanol (20 mL), was added sodium borohydride (0.27 g, 7.32 mmol). The reaction mixture was allowed to warm to room temperature over 2 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic extracts were washed with brine, dried (MgSO4), and concentrated under reduced pressure to afford an oil. To a solution of the oil in toluene (25 mL), was added diphenylphosphoryl azide (1.26 mL, 5.85 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (881 μL, 5.85 mmol). The reaction mixture was stirred at 100° C. for 3 hours. The reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate and washed with water, brine, dried (magnesium sulphate), filtered and concentrated. The crude material was purified by silica gel chromatography eluting with 0-10% ethyl acetate in iso-hexane to afford the title compound (1.62 g, 92% over 2 steps).

1. extractionextracted with ethyl acetate
2. washThe organic extracts were washed with brine
3. dry with materialdried (MgSO4)
4. concentrationconcentrated under reduced pressure
5. customto afford an oil
6. temperatureto cool to room temperature
7. washwashed with water, brine
8. dry with materialdried (magnesium sulphate)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe crude material was purified by silica gel chromatography
12. washeluting with 0-10% ethyl acetate in iso-hexane