反应详情

14 grams (50 mmol) of ethyl 4-hydroxy-7-trifluoromethyl-3-quinolinecarboxylate was suspended in 400 ml THF, and 9.5 grams (250 mmol) lithium aluminum hydride were added slowly. The mixture was stirred at room temperature for 12 hours, cooled, 250 ml water was added and the resulting mixture was stirred overnight. The solvent was thereafter evaporated, and water (300 ml) was again added. The aqueous suspension was extracted with dichloromethane. The organic extract was evaporated, and the remaining residue was purified by column chromatography on silica gel, using a 9:1 mixture of ethylacetate and methanol as eluent, to yield 4-hydroxy-7-trifluoromethyl-3-(hydroxymethyl)-quinoline (12 grams, 82% yield).

1. temperaturecooled
2. stirringthe resulting mixture was stirred overnight
3. customThe solvent was thereafter evaporated
4. additionwater (300 ml) was again added
5. extractionThe aqueous suspension was extracted with dichloromethane
6. extractionThe organic extract
7. customwas evaporated
8. customthe remaining residue was purified by column chromatography on silica gel
9. additiona 9:1 mixture of ethylacetate and methanol as eluent