反应详情

To a mixture of Meldrum's acid (688 mg) and 4-phenylethynylbenzoic acid (955 mg) in methylene chloride (30 mL) was added a solution of 4-dimethylaminopyridine (830 mg) and N, N′-dicyclohexylcarbodiimide (976 mg) in methylene chloride (15 mL) under ice-cooling, and the mixture was stirred at room temperature for 66 hr. Insoluble material was removed by filtration, and the filtrate was washed with 10% potassium hydrogen sulfate (30 mL) and saturated brine and concentrated under reduced pressure. The residue was dissolved in acetic acid (5 mL), and the solution was cooled to 0° C. Sodium borohydride (408 mg) was added, and the mixture was stirred at room temperature for 6 hr. Water (50 mL) was added to the reaction mixture, and the mixture was extracted with methylene chloride (50 mL×2). The organic layer was washed with saturated brine and concentrated under reduced pressure. The residue was washed with isopropanol, and the resulting precipitate was collected by filtration to give the title compound (654 mg) as a white solid.

1. temperaturecooling
2. customInsoluble material was removed by filtration
3. washthe filtrate was washed with 10% potassium hydrogen sulfate (30 mL) and saturated brine
4. concentrationconcentrated under reduced pressure
5. dissolutionThe residue was dissolved in acetic acid (5 mL)
6. temperaturethe solution was cooled to 0° C
7. additionSodium borohydride (408 mg) was added
8. stirringthe mixture was stirred at room temperature for 6 hr
9. additionWater (50 mL) was added to the reaction mixture
10. extractionthe mixture was extracted with methylene chloride (50 mL×2)
11. washThe organic layer was washed with saturated brine
12. concentrationconcentrated under reduced pressure
13. washThe residue was washed with isopropanol
14. filtrationthe resulting precipitate was collected by filtration