Carbon Tetrachloride → octahydro-1-(1,5-dimethylhexyl)-7a-methyl-4H-inden-4-one

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

[1R-(1β(R*),3aα,7aβ)] octahydro-1-(1,5-dimethylhexyl)-7a-methyl-4H-inden-4-ol (2.66 g, 0.01 mol) (prepared as described in Inhoffen et al., F. Chem. Ber. 1957, 90.664), sodium metaperiodate (7.48 g), ruthenium (III) chloride hydrate (0.207 g, 10 mol %), carbon tetrachloride (40 ml), acetonitrile (40 ml) and pH 7.0 buffer (monobasic potassium phosphate-sodium hydroxide, 0.05M in water) (52 ml) were stirred vigorously by mechanical stirring for 68 hours at 45° C. After this period, 30 ml water was added and this was extracted with methylene chloride (2×40 ml). The extracts were combined, dried over magnesium sulfate and evaporated. Flash chromatography (hexanes -EtOAc=20:1, later 4:1) afforded 0.73 g (26%) of [1R-(1β(R*), 3aα, 7aβ)]octahydro-1-(1,5-dimethylhexyl)-7a-methyl-4H-inden-4-one, the compound of formula III, and 1.15 g (41%) of [1R-(1β(R*), 3aα, 4β, 7aβ)]octahydro-1-(5-hydroxy-1,5-dimethylhexyl)-7a-methyl-4H-inden-4-one, the compound of formula I, as a pale yellow oil which solidifies upon standing in the freezer.

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