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

HRID 612308Notes

Reaction equation

HRID 612308 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 (1.95 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 (4 H, m), 3.85 (3 H, s) and 4.55-4.8 (2 H, m).

Workup

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

Sources & evidence

ORD record
ord-602f631583b54b2b8b57e542c2de374a
Source dataset
uspto-grants-1999_12
Patent number
US06001997

Reaction notes

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