反应详情

To a stirred solution of 4-bromo-3,5-dimethylphenol (40.87 g, 203.3 mmol) and propiolic acid (20.91 g, 298.5 mmol) in CH2Cl2 (400 mL) was added DCC (50.78 g, 246.1 mmol) in CH2Cl2 (100 mL) and DMAP (0.82 g, 6.7 mmol) at 0° C. The mixture was stirred at room temperature for 3 h and filtered. The filtrate was concentrated and purified by silica gel column chromatography (hexanes:EtOAc:CH2Cl2=20:1:10). The fractions containing the desired compound were concentrated. To the concentrate added hexane and the precipitated solid was collected by filtration. The solid was washed with hexane and dried to give the title compound 6-1 (26.12 g, 51% yield) as a white solid.

1. filtrationfiltered
2. concentrationThe filtrate was concentrated
3. custompurified by silica gel column chromatography (hexanes:EtOAc:CH2Cl2=20:1:10)
4. additionThe fractions containing the desired compound
5. concentrationwere concentrated
6. additionTo the concentrate added hexane
7. filtrationthe precipitated solid was collected by filtration
8. washThe solid was washed with hexane
9. customdried