Water → cis-1,2-Cyclooctanediol

HRID 2104357Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2104357
[CH:1]1CC[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.C[N+]1([O-])[CH2:15][CH2:14][O:13]CC1.[OH2:17]>C(#N)C.[Os](=O)(=O)(=O)=O>[C@@H:14]1([OH:13])[CH2:15][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C@@H:1]1[OH:17]

Komponenten

6

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

Cyclooctene (4.41 g) was dissolved in acetonitrile (45 mL) and water (15 mL), and to the solution were added N-methylmorpholine N-oxide (5.15 g), microencapsulated osmium tetraoxide (1 g, 10% osmium tetraoxide content), followed by stirring at 40-50° C. for 21 hours. Any insoluble microencapsulated osmium was filtered off, and was washed with acetonitrile. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel flash column chromatography (hexane:ethyl acetate=1:1), to thereby give the title compound (4.97 g).

Aufarbeitung

  1. filtrationAny insoluble microencapsulated osmium was filtered off
  2. washwas washed with acetonitrile
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel flash column chromatography (hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-4af616c19fea4bdabdafcb62035d3786
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576135B2

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