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

HRID 376604Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 376604
[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 (1.95g) and 5% rhodium on carbon (400mg) in ethyl acetate (50ml) was hydrogenated until hydrogen uptake ceased. The catalyst was filtered off and washed with ethyl acetate. The combined filtrates were evaporated to give (2.00g) of the title compound: vmax (film) 3170, 1765 and 1720cm-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-57d61691c31641d4899d2eb91a874218
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06020329

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