tetrahydro-3-hexyl-4-oxo-(R)-6-undecyl-2H-pyran-2-one → (3S,4S,6R)-3-Hexyltetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one

HRID 2106843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2106843
[CH2:1]([C@@H:7]1[C:12](=[O:13])[CH2:11][CH:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:9][C:8]1=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]>C(OCC)(=O)C.O=[Pt]=O>[CH2:1]([C@H:7]1[C@@H:12]([OH:13])[CH2:11][C@@H:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:9][C:8]1=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Komponenten

4

Edukt 1

HCID 67855749tetrahydro-3-hexyl-4-oxo-(R)-6-undecyl-2H-pyran-2-one

Produkt 1

HCID 11013671(3S,4S,6R)-3-Hexyltetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(M)(c) 8 g of an isomer mixture of tetrahydro-3-hexyl-4-oxo-(R)-6-undecyl-2H-pyran-2-one were dissolved in 2 1 of ethyl acetate and 3 g of PtO2 were added. The mixture was then hydrogenated (50 bar) for 12 hours. The catalyst was filtered off and the solution was evaporated. After recrystallization there were obtained 7 g of (3S,4S,6R)-tetrahydro-3-hexyl-4-hydroxy-6-undecyl-2H-pyran-2-one, m.p. 108°-109° C.

Aufarbeitung

  1. additionwere added
  2. filtrationThe catalyst was filtered off
  3. customthe solution was evaporated
  4. customAfter recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-1731c202461f4ca89f4d9f6399e4e17a
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04931463

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