反应详情

To a suspension of 0.96 g of sodium hydride in 10 mL of dry DMF was added 3.6 g of 4-chloro-8-fluoroquinoline. The mixture was cooled in an ice/water bath, and 3.3 g of 2-[4-(1-methylethyl)phenyl]ethyl alcohol was added. The mixture was stirred overnight, then diluted with ice and water. The pH was adjusted to 7, then the product was extracted into CH2Cl2. The CH2Cl2 layer was separated, filtered, and evaporated in vacuo. An azeotrope with xylene was formed to facilitate removal of residual DMF. The residue was chromatographically purified on a silica gel column, eluting with CH2Cl2, →5% EtOAc/CH2Cl2 →10% EtOAc/CH2Cl2. The fractions containing product were combined and evaporated to give an oil, which crystallized on adding ether. Recrystallization yielded 2.5 g of title product. M.P. 56°-60° C.

1. temperatureThe mixture was cooled in an ice/water bath
2. extractionthe product was extracted into CH2Cl2
3. customThe CH2Cl2 layer was separated
4. filtrationfiltered
5. customevaporated in vacuo
6. customAn azeotrope with xylene was formed
7. customremoval of residual DMF
8. customThe residue was chromatographically purified on a silica gel column
9. washeluting with CH2Cl2, →5% EtOAc/CH2Cl2 →10% EtOAc/CH2Cl2
10. additionThe fractions containing product
11. customevaporated
12. customto give an oil, which
13. customcrystallized
14. additionon adding ether
15. customRecrystallization