Ethanol → Methyl 3-(5-ethyl-2-furyl)propanoate

HRID 1377817Notes

Reaction equation

HRID 1377817 reaction equation
[CH2:1]([C:3]1[O:7][C:6]([CH:8]=[CH:9][C:10]([O-:12])=[O:11])=[CH:5][CH:4]=1)[CH3:2].[CH2:13](O)C>[Pd]>[CH2:1]([C:3]1[O:7][C:6]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 702EthanolHCID 867512273-(5-Ethyl-2-furanyl)propenoate

Product 1

HCID 14982790Methyl 3-(5-ethyl-2-furyl)propanoate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a suspension of ethanol (200 mL) and 300 mg of 5% palladium on carbon was added 14.8 g (82.1 mmol) of 3-(5-ethyl-2-furanyl)propenoate at room temperature and the mixture was placed on a Paar hydrogenator and hydrogenated with H2. Palladium on carbon was filtered off bypassing the reaction mixture through a filter aid, Super-Cel™ and the residue was washed with ethanol several times. The filtrate was concentrated in vacuo, methylene chloride was added to the residue and the solvent was removed in vacuo to afford 14.9 g methyl 3-(5-ethyl-2-furanyl)propanoate. This ester was used without further purification.

Workup

  1. filtrationPalladium on carbon was filtered off bypassing the reaction mixture through a filter aid, Super-Cel™
  2. washthe residue was washed with ethanol several times
  3. concentrationThe filtrate was concentrated in vacuo, methylene chloride
  4. additionwas added to the residue
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8634a87b16184a18b7ebccb08dcbab84
Source dataset
uspto-grants-1997_09
Patent number
US05665763

Reaction notes

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