Chloroform → HCID 29923590, compound

Participants

Reaction Steps

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).

Provenance & Evidence