5-(Methoxycarbonyl)furan-2-carboxylic acid → 5-(Methoxycarbonyl)oxolane-2-carboxylic acid

HRID 1421824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1421824
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]([C:10]([OH:12])=[O:11])=[CH:8][CH:9]=1)=[O:4].[H][H]>C(OCC)(=O)C.[Rh]>[CH3:1][O:2][C:3]([CH:5]1[O:6][CH:7]([C:10]([OH:12])=[O:11])[CH2:8][CH2:9]1)=[O:4]

Komponenten

5

Edukt 2

HCID 114351815-(Methoxycarbonyl)furan-2-carboxylic acidHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 134258045-(Methoxycarbonyl)oxolane-2-carboxylic acidAusbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23948RhodiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of furan-2,5-dicarboxylic acid monomethyl ester (1.95 g) and 5% rhodium on carbon (400 mg) in ethyl acetate (50 ml) was hydrogenated until hydrogen uptake ceased. The catalyst was filtered off and washed with ethyl acetate. The combined filtrates were evaporated to give (2.00 g) of the title compound: νmax (film) 3170, 1765 and 1720 cm-1 ; δH (CDCl3) 1.95-2.65 (4H, m), 3.85 (3H, s) and 4.55-4.8 (2H, m).

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethyl acetate
  3. customThe combined filtrates were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-591f113ceadb40adb7ada15fc63b2db3
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06077952

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