反应详情

3.00 g (9.6 mmol) of methyl 2-(4-methylsulfonylphenacyl)acetoacetate [prepared as described in step (ii) above] were dissolved in 100 ml of acetic acid and 0.97 g (8.7 mmol) of 4-fluoroaniline was added to the resulting solution. The resulting mixture was then heated under reflux for 5 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, a saturated aqueous solution of sodium hydrogencarbonate was added to the residue and the mixture was extracted with ethyl acetate. The organic extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure. The residue was applied to a silica gel chromatography column and eluted with a 1:2 by volume mixture of ethyl acetate and hexane, to give 3.10 g of the title compound as a white powder (yield 92%), melting at 154-155° C.

1. temperatureThe resulting mixture was then heated
2. temperatureunder reflux for 5 hours
3. customAt the end of this time, the solvent was removed by distillation under reduced pressure
4. additiona saturated aqueous solution of sodium hydrogencarbonate was added to the residue
5. extractionthe mixture was extracted with ethyl acetate
6. extractionThe organic extract
7. washwas washed with a saturated aqueous solution of sodium chloride
8. dry with materialdried over anhydrous magnesium sulfate
9. customThe solvent was then removed by distillation under reduced pressure
10. washeluted with a 1:2 by volume mixture of ethyl acetate and hexane