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

HRID 1421819Notes

Reaction equation

HRID 1421819 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 (3.65 g, 28.97 mmol) in ethyl acetate (60 ml) was hydrogenated over 5% rhodium on carbon (250 mg) 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 (3.67 g, 97%); νmax (CH2Cl2) 3384, 3359, 1775, 1724 and 1355 cm-1 ; δH (CDCl3, 250 MHz) 1.35 (3H, d, J 6.1 Hz), 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, 4.7 Hz). [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-f6544927d35c4c838dfe917d18c4c749
Source dataset
uspto-grants-2000_06
Patent number
US06077952

Reaction notes

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