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

HRID 256770

Reaktionsgleichung

[CH3:1][CH:2]([CH:9]1[C:17]2([CH3:18])[CH:12]([CH:13]([OH:19])[CH2:14][CH2:15][CH2:16]2)[CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].I([O-])(=O)(=O)=O.[Na+].C(Cl)(Cl)(Cl)Cl.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[OH-].[Na+]>O.O.[Ru](Cl)(Cl)Cl.C(#N)C>[CH3:1][CH:2]([CH:9]1[C:17]2([CH3:18])[CH:12]([C:13](=[O:19])[CH2:14][CH2:15][CH2:16]2)[CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:7])[CH3:8]

Komponenten

Reaktionsbedingungen

Temperatur: 45 °C

Versuchsvorschrift

[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.

Aufarbeitung

waitAfter this period
extractionthis was extracted with methylene chloride (2×40 ml)
dry with materialdried over magnesium sulfate
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-deedacd342634676b8aa7871fd165e02
Quelldatensatz: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05258559

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