(E)-Ethyl 3-(2-furyl)acrylate → Ethyl 2-furanpropionate

HRID 1092001Notes

Reaction equation

HRID 1092001 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:6]=[CH:7]/[C:8]([O:10][CH2:11][CH3:12])=[O:9]>C(O)C.[Pd]>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 1

HCID 699489(E)-Ethyl 3-(2-furyl)acrylate

Product 1

HCID 61450Ethyl 2-furanpropionate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

A cis/trans mixture of ethyl (E)-3-(2-furyl)prop-2-enoate (15.5 g, 93.27 mmol, 1 eq) was stirred in ethanol (120 ml) containing 10% palladium on charcoal (775 mg, 5% by w). The reaction mixture was stirred under hydrogen for 4 h. A further quantity of 10% Pd/C (775 mg, 5% by w) was added. The reaction was stirred under hydrogen for an additional 95 mins. The reaction was filtered and evaporated under reduced pressure. The crude product was purified by silica column chromatography eluting with 20% ethyl acetate in hexanes. The desired fractions were evaporated under reduced pressure and ethyl 3-(2-furyl)propanoate was obtained as a clear oil (3.69 g, 24% yield).

Workup

  1. stirringThe reaction was stirred under hydrogen for an additional 95 mins
  2. filtrationThe reaction was filtered
  3. customevaporated under reduced pressure
  4. customThe crude product was purified by silica column chromatography
  5. washeluting with 20% ethyl acetate in hexanes
  6. customThe desired fractions were evaporated under reduced pressure

Sources & evidence

ORD record
ord-6edfcc6f6a9f42488e3b47331eab333e
Source dataset
uspto-grants-2012_03
Patent number
US08129391B2

Reaction notes

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