反应详情

温度

95 °C

To a mixture of methyl 4-(2-tetrahydro-2H-pyranoxy methyl)benzoyl-pyruvate (0.17 g, 0.53 mmol), 4-isoxazol-3-ylaniline (0.085 g, 0.53 mmol) and acetic acid (1 mL), cyclohexane carboaldehyde (0.064 mL, 0.53 mmol) was added. The mixture was stirred at 95° C. for 0.5 hr, and cooled to r.t. The precipitate was collected by filtration and washed with ethyl acetate to give crude precursor. Methanol (5 mL), THF (5 mL) and pyridinium p-toluenesulfonate (0.027 g, 0.11 mmol) were added to the precursor, and the mixture was stirred at 60° C. for 0.5 hr. Water was added to the mixture, which was then extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give 5-cyclohexyl-3-hydroxy-4-(4-hydroxy methylbenzoyl)-1-(4-isoxazol-3-yl-phenyl)-1,5-dihydropyrrol-2-one (0.022 g, 9%) as colorless crystals.

1. additionwas added
2. temperaturecooled to r.t
3. filtrationThe precipitate was collected by filtration
4. washwashed with ethyl acetate
5. customto give crude precursor
6. stirringthe mixture was stirred at 60° C. for 0.5 hr
7. extractionwas then extracted with chloroform
8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe residue was recrystallized from ethyl acetate