Reaktion #790866

ord-fcb88f9fae254b8a9976d6a1fbc8abbd

Reaktionsgleichung

O
H2O
CCCCCCCCCCCC1CC(O)[C@@H](CCCCCC)C(=O)O1
tetrahydro-3-hexyl-4-hydroxy-(R)-6-undecyl-2H-pyran-2-one
CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones' reagent
→
CCCCCCCCCCCC1CC(=O)[C@@H](CCCCCC)C(=O)O1
tetrahydro-3-hexyl-4-oxo-(R)-6-undecyl-2H-pyran-2-one

Edukte

O
H2O
—
diastereomer mixture
CCCCCCCCCCCC1CC(O)[C@@H](CCCCCC)C(=O)O1
tetrahydro-3-hexyl-4-hydroxy-(R)-6-undecyl-2H-pyran-2-one
CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones' reagent

Reagenzien

Keine

Lösungsmittel

CC(C)=O
acetone

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigedoes not exceed 25° C
  2. 2
    SonstigeThe lactone Precipitates out and
  3. 3
    Filtrationis filtered off
  4. 4
    SonstigeAfter recrystallization in ether/n-hexane there

Vorschrift

3 g of a diastereomer mixture of tetrahydro-3-hexyl-4-hydroxy-(R)-6-undecyl-2H-pyran-2-one are dissolved in 300 ml of acetone. 3 ml of Jones' reagent are added dropwise while stirring in such a manner that the temperature does not exceed 25° C. After 3 hours the reaction mixture is poured into 700 ml of H2O. The lactone Precipitates out and is filtered off. After recrystallization in ether/n-hexane there are obtained 1.7 g of tetrahydro-3-hexyl-4-oxo-(R)-6-undecyl-2H-pyran-2-one, m.p. 112.5°-113.5° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04983746uspto-grants-1991_01