反应详情

温度

0 °C

A crystal of iodine was added to 0.45 gm (18.7 mMol) magnesium turnings covered with 6 mL tetrahydrofuran. To this mixture were added 5-6 drops of dibromoethane and the mixture was heated with a heat gun to initiate the reaction. Once the iodine color disappeared, 2 mL (15 mMol) 1-methyl-4-chloropiperidine were added and heating continued for an additional 30 seconds. After the exothermic reaction no longer maintained reflux temperature, the reaction mixture was heated at reflux for 30 minutes and was then cooled to 0° C. To the cold mixture was added the previously prepared N-methyl-N-methoxy 2-(4-acetamidophenoxy)acetamide and the resulting mixture stirred for 30 minutes at 0° C. and then an additional hour after warming to room temperature. The reaction was quenched by the addition of water and the resulting mixture extracted well with ethyl acetate. The combined organic extracts were washed saturated aqueous ammonium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography, eluting with dichloromethane containing 5% methanol. Fractions shown to contain product were combined and concentrated under reduced pressure to provide 0.90 gm (47%) of the desired ketone.

1. temperaturethe mixture was heated with a heat gun
2. customthe reaction
3. temperatureheating
4. customAfter the exothermic reaction
5. temperatureno longer maintained
6. temperaturereflux temperature
7. temperaturethe reaction mixture was heated
8. temperatureat reflux for 30 minutes
9. temperaturean additional hour after warming to room temperature
10. customThe reaction was quenched by the addition of water
11. extractionthe resulting mixture extracted well with ethyl acetate
12. washThe combined organic extracts were washed saturated aqueous ammonium chloride
13. dry with materialdried over magnesium sulfate
14. concentrationconcentrated under reduced pressure
15. washeluting with dichloromethane containing 5% methanol
16. concentrationconcentrated under reduced pressure