2-Furancarboxylic acid, 5-methyl- → 5-Methyloxolane-2-carboxylic acid

HRID 376598

Reaktionsgleichung

Reaktionsgleichung von HRID 376598
[CH3:1][C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[H][H]>C(OCC)(=O)C.[Rh]>[CH3:1][CH:2]1[O:6][CH:5]([C:7]([OH:9])=[O:8])[CH2:4][CH2:3]1

Komponenten

5

Edukt 2

HCID 747102-Furancarboxylic acid, 5-methyl-HCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 187800675-Methyloxolane-2-carboxylic acidAusbeute 97,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23948RhodiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 5-methyl-2-furoic acid (3.65g, 28.97mmol) in ethyl acetate (60ml) was hydrogenated over 5% rhodium on carbon (250mg) until hydrogen uptake ceased. The catalyst was filtered off and washed with ethyl acetate. The combined filtrates were concentrated in vacuo to yield the title compound as a pale yellow oil (3.67g, 97%); vmax (CH2Cl2) 3384, 3359, 1775, 1724 and 1355cm-1 ; δH (CDCl3, 250MHz) 1.35 (3H, d, J 6.1Hz), 1.53 (1H, m), 2.09 (1H, m), 2.17-2.40 (2H, m), 4.21 (1H, m) and 4.46 (1H, dd, J 8.9, 4.7Hz). [Mass spectrum: +ve ion (ammonia) MNH4+ (148)].

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethyl acetate
  3. concentrationThe combined filtrates were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5fe28c5f82214b858e2873896da57487
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06020329

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