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

HRID 376598

Reaction equation

HRID 376598 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

HCID 187800675-Methyloxolane-2-carboxylic acidYield 97.3%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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)].

Workup

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

Sources & evidence

ORD record
ord-5fe28c5f82214b858e2873896da57487
Source dataset
uspto-grants-2000_02
Patent number
US06020329

Linked notes

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