反应详情

A solution of 3-(8-nonenyl)-1-methylthymine (2.63 g, 9.9 mmol), prepared above, 4-methylmorpholine-N oxide (1.39 g, 12 mmol), and potassium osmate (IV) dihydrate (7 mg, 2×10-5 mol) in acetone (20 ml) and water (10 ml) was stirred for 18 hours. After addition of a saturated aqueous solution of sodium hydrosulfite (10 ml) and 15 minutes of stirring, the reaction mixture was extracted with dichloromethane (50 ml) and with two 50 ml aliquots of dichloromethane/20% methanol. The combined organic layers were washed with water (15 ml) and saturated aqueous salt solution (15 ml), and then dried over sodium sulfate. The solvent was evaporated under vacuum, leaving a white solid residue. Recrystallization of the solid in ethanol yielded 2.68 g of 3-(8,9-dihydroxynonyl)-1-methylthymine (91% yield).

1. stirringof stirring
2. extractionthe reaction mixture was extracted with dichloromethane (50 ml) and with two 50 ml aliquots of dichloromethane/20% methanol
3. washThe combined organic layers were washed with water (15 ml) and saturated aqueous salt solution (15 ml)
4. dry with materialdried over sodium sulfate
5. customThe solvent was evaporated under vacuum
6. customleaving a white solid residue
7. customRecrystallization of the solid in ethanol