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

HRID 376604Notes

Reaction equation

HRID 376604 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

HCID 134258045-(Methoxycarbonyl)oxolane-2-carboxylic acidYield 100.2%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-57d61691c31641d4899d2eb91a874218
Source dataset
uspto-grants-2000_02
Patent number
US06020329

Reaction notes

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