Chloroform → HCID 29923590, compound

Participants

Reaction Steps

A mixture of (2R)-6-hydroxyhexane-1,2-diyl dinitrate (13.5 g, 60.2 mmol) and sodium periodate (38.74 g, 181 mmol) was suspended in a mixture of water (250 mL), acetonitrile (250 mL), and chloroform (250 mL). Ruthenium oxide hydrate (0.813 g, 6.11 mmol) was then added, turning the reaction bright yellow. After 16 hours, the reaction mixture was concentrated in vacuo to remove the organic solvents. The residue was extracted with dichloromethane (3×200 mL), and the combined organic extracts were washed with brine, dried (magnesium sulfate), and concentrated in vacuo to afford the crude product. Chromatography over silica eluting with 0-5% methanol in dichloromethane afforded the title compound as a yellow liquid. 1H NMR (500 MHz, CDCl3) 5.26-5.33 (m, 1H), 4.76 (dd, J=3.1, 12.9 Hz, 1H), 4.49 (dd, J=6.4, 13.0 Hz, 1H), 2.45 (t, J=5.8 Hz, 2H), 1.72-1.88 (m, 4H).

Provenance & Evidence