Water → cis-1,2-Cyclooctanediol

HRID 902842Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 902842
[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

Edukt 3

HCID 962WaterHCID 136091-CycloocteneHCID 82029Methyl morpholine oxide

Produkt 1

HCID 10888034cis-1,2-Cyclooctanediol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

Cyclooctene (4.41 g) was dissolved in acetonitrile (45 ml) and water (15 ml), and to the solution N-methylmorpholine N-oxide (5.15 g) and microcapsulated osmium tetroxide (1 g, containing 10% osmium tetroxide) were added, and the mixture was stirred at 40 to 50° C. for 21 hours. Insoluble microcapsulated osmium tetroxide was removed by filtration, and washed with acetonitrile, and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1) to obtain the title compound (4.97 g).

Aufarbeitung

  1. customInsoluble microcapsulated osmium tetroxide was removed by filtration
  2. washwashed with acetonitrile
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-23b67f7db84f476aba935d7a7d42e6c8
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365205B2

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