反应详情

A mixture of (2R)-6-hydroxyhexane-1,2-diyl dinitrate (intermediate 2, 13.5 g, 60.2 mmol) and sodium periodate (38.74 g, 181 mmol) was suspended in water (250 mL)/acetonitrile (250 mL)/chloroform (250 mL). Ruthenium oxide hydrate (0.813 g, 6.11 mmol) was then added, turning the reaction into bright yellow. After 16 hours, the reaction mixture was concentrated in vacuo to remove the organic solvents. It was extracted with dichloromethane (3×200 mL), and the combined organic extracts were washed with brine, dried (magnesium sulfate), filtered, and concentrated in vacuo to afford the crude product. Chromatography over silica eluting with methanol/dichloromethane afforded (5R)-5,6-bis(nitrooxy)hexanoic acid as a yellow liquid. 1H NMR (500 MHz, CDCl3) δ 5.25-5.35 (m, 1H), 4.76 (dd, J=3.1, 12.9 Hz, 1H), 4.49 (dd, J=6.4, 13.0 Hz, 1H), 2.4-2.5 (m, 2H), 1.7-1.9 (m, 4H).

1. customthe reaction into bright yellow
2. concentrationthe reaction mixture was concentrated in vacuo
3. customto remove the organic solvents
4. extractionIt was extracted with dichloromethane (3×200 mL)
5. washthe combined organic extracts were washed with brine
6. dry with materialdried (magnesium sulfate)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto afford the crude product