Water → HCID 15417111, compound

Participants

Reaction Steps

1.43 g (12 mmol) of thionyl chloride were slowly added to 3.30 g (10 mmol) of the diol 5 in 70 ml of dry tetrachloromethane under an argon atmosphere, and the mixture was then refluxed for 90 minutes. After removal of the solvent in a rotary evaporator, the residue was taken up in a mixture of tetrachloromethane (40 ml), acetonitrile (40 ml) and water (60 ml) and, at 0° C., 15 mg (72 μmol) of RuCl3*3H2O and 4.28 g (20 mmol) of sodium periodate were added. The mixture was then left to stir at room temperature for one hour, and then 50 ml of water were added to the suspension. Subsequent extraction with diethyl ether (3×75 ml) and washing of the organic phase with saturated NaCl solution (100 ml), followed by drying (Na2SO4), resulted in a residue which on column chromatography (n-hexane:AcOEt=2:1, Rf=0.20) afforded compound 7 in a yield of 3.37 g (86%).

Provenance & Evidence