反应详情

210 Milligrams of 4-acetoxy-6-s-butyl-8-formyl-2,3-dimethylquinoline obtained in Example 33 was dissolved in 4 ml of methanol, to which 7 mg of sodium borohydride dissolved in 4 ml of methanol was added dropwise and the mixture was stirred at room temperature for 1 minute. After the addition of 20 ml of water, the reaction mixture was extracted with ethyl acetate. The resultant organic layer was washed with a saturated brine and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, the resultant crude product was purified by column chromatography on silica gel (WAKOGEL® C-200) eluting with n-hexane/ethyl acetate (10:1) to obtain 186 mg of 4-acetoxy-6-s-butyl-8-hydroxymethyl-2,3-dimethylquinoline (yield 84%). Its NMR spectral data are shown in the following Table 2.

1. additionwas added dropwise
2. extractionthe reaction mixture was extracted with ethyl acetate
3. washThe resultant organic layer was washed with a saturated brine
4. dry with materialdried over anhydrous sodium sulfate
5. customAfter the solvent was evaporated under reduced pressure
6. customthe resultant crude product was purified by column chromatography on silica gel (WAKOGEL® C-200)
7. washeluting with n-hexane/ethyl acetate (10:1)