反应详情

o-Anisidine (2.34 ml, 20 mmol) was dissolved in toluene (60 ml) to which were subsequently added, with cooling in an ice bath, pyridine (4.58 ml, 60 mmol), p-toluenesulfonyl chloride (3.89 g, 20 mmol) and a catalytically effective amount of 4-dimethylaminopyridine. After 2.5 hours of stirring at room temperature, the resulting reaction solution was mixed-with water (50 ml), extracted with ethyl acetate and then washed with water, 10% sodium hydroxide aqueous solution, 1N hydrochloric acid, water and saturated brine in that order. After drying on anhydrous magnesium sulfate and removing the solvent by evaporation, the resulting orange solid was dissolved in ethyl acetate (50 ml), adsorbed to anhydrous magnesium sulfate (20 g), eluted with ether and then subjected to evaporation to remove the solvent. The resulting colorless solid which was then washed with an ether-hexane (1:1) mixture solution to obtain 3.44 g (62.0%) of the title compound in the form of colorless prism crystals.

1. additionwere subsequently added
2. temperaturewith cooling in an ice bath
3. customthe resulting reaction solution
4. extractionextracted with ethyl acetate
5. washwashed with water, 10% sodium hydroxide aqueous solution, 1N hydrochloric acid, water and saturated brine in that order
6. dry with materialAfter drying on anhydrous magnesium sulfate
7. customremoving the solvent
8. customby evaporation
9. dissolutionthe resulting orange solid was dissolved in ethyl acetate (50 ml)
10. washeluted with ether
11. customsubjected to evaporation
12. customto remove the solvent
13. washThe resulting colorless solid which was then washed with an ether-hexane (1:1) mixture solution