反应详情

Methyl 3-acetyl-4-hydroxybenzoate (200 mg, 1.03 mmol), acetone (151 μL, 2.06 mmol) and pyrrolidine (25.6 μL, 0.31 mmol) were mixed in toluene (515 μL) and stirred at room temperature for 1 hour. It was then heated to 100° C. for 5 hours, allowed to cool to room temperature, diluted with EtOAc (50.0 mL) and poured into ice. The two layers were separated. The organic layer was washed with 2 N aqueous HCl (10.0 mL), 2 N aqueous NaOH (10.0 mL), water (10.0 mL), dried over Na2SO4, filtered and concentrated under vacuum. The crude mixture was purified by silica gel chromatography eluting with 0-30% EtOAc/hexanes to give the desired product as a pale-yellow oil.

1. temperatureIt was then heated to 100° C. for 5 hours
2. temperatureto cool to room temperature
3. additionpoured into ice
4. customThe two layers were separated
5. washThe organic layer was washed with 2 N aqueous HCl (10.0 mL), 2 N aqueous NaOH (10.0 mL), water (10.0 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under vacuum
9. customThe crude mixture was purified by silica gel chromatography
10. washeluting with 0-30% EtOAc/hexanes