5-(Methoxymethyl)furan-2-carboxylic acid → HCID 18780016, compound

HRID 376583

Reaction equation

HRID 376583 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[O:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6][CH:5]=1.[H][H]>C(OCC)(=O)C.[Rh]>[CH3:1][O:2][CH2:3][CH:4]1[O:8][CH:7]([C:9]([OH:11])=[O:10])[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 11252275-(Methoxymethyl)furan-2-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 18780016HCID 18780016, compoundYield 102.5%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-methoxymethylfuran-2-carboxylic acid (3.10g) in ethyl acetate (40ml) was hydrogenated over 5% rhodium on carbon (200mg) until hydrogen uptake ceased. The catalyst was filtered off and washed with ethyl acetate. The combined filtrates were evaporated to give the title compound as a colourless oil (3.26g); vmax (film) 1750cm-1 ; δH (CDCl3) 1.75-2.1 (2H,m), 2.1-2.6(2H,m,), 3.45 (3H,s), 3.47 (1H,dd, J 3 and 10 Hz), 3.74 (1H,dd, J 4 and 10Hz), 4.15-4.43 (1H,m) and 4.43-4.63 (1H,m).

Workup

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

Sources & evidence

ORD record
ord-dbb2005aa4f24ef994b988d348421e78
Source dataset
uspto-grants-2000_02
Patent number
US06020329

Linked notes

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