反应详情

Trifluoromethanesulfonic anhydride (28.5 mL) was added dropwise to a solution of 7-hydroxyquinoline (22.0 g) in anhydrous pyridine (100 mL) cooled on ice. After 10 minutes, the mixture was warmed to ambient temperature and stirred overnight. The mixture was poured into 1000 mL of ice-cold 1 N HCl and extracted three times with 500 mL of ether. The combined organic extracts were washed once with water and once with brine, then dried over MgSO4, filtered, and evaporated. The crude product was chromatographed on silica gel (1:1 ethyl acetate/hexanes), then crystallized from hot hexane, yielding 32.3 g of product as pale yellow crystals. 1H-NMR (CDCl3): δ 8.98 (1H, dd, J=1.6, 4.4 Hz), 8.21 (1H, d, J=7.6 Hz), 8.03 (1H, d, J=2.4 Hz), 7.91 (1H, d, J=8.8 Hz), 7.48 (2H, m). 13C-NMR (CDCl3): δ 151.4, 149.9, 146.9, 137.3, 130.4, 127.5, 122.3, 121.1, 120.2, 118.7 (q, JCF=320 Hz).

1. temperaturecooled on ice
2. extractionextracted three times with 500 mL of ether
3. washThe combined organic extracts were washed once with water and once with brine
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customevaporated
7. customThe crude product was chromatographed on silica gel (1:1 ethyl acetate/hexanes)
8. customcrystallized from hot hexane