Ethyl-3-(5'-fluoro-2'-methoxyphenyl)acrylate → Ethyl 3-(5'-fluoro-2'-methoxyphenyl)propionate

HRID 1919513Notes

Reaction equation

HRID 1919513 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH:5]=[CH:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[O:14][CH3:15])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[O:14][CH3:15])[CH3:2]

Participants

4

Reactant 1

HCID 67499726Ethyl-3-(5'-fluoro-2'-methoxyphenyl)acrylate

Product 1

HCID 20244908Ethyl 3-(5'-fluoro-2'-methoxyphenyl)propionateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl-3-(5′-fluoro-2′-methoxyphenyl)acrylate (6.0 g, 27 mmol) in ethanol (100%, 80 mL) under Ar was added Pd/C (10%, 250 mg) very carefully and the flask containing the mixture was evacuated and purged with H2 three time each. Then a H2 balloon was attached to the flask and charged with H2 and the reaction was allowed to go for 20 h at room temperature. Then the reaction mixture was filtered through a pad of silica eluted with mixed solvent of EtOAc and Hexane (1:1). The crude product that obtained by removal of the solvent in vacuo was purified by flash column chromatography (10% EtOAc in hexane, Rf=0.20) to give the product (5.8 g, 95%).

Workup

  1. additionthe flask containing the mixture
  2. customwas evacuated
  3. custompurged with H2 three time each
  4. additioncharged with H2
  5. filtrationThen the reaction mixture was filtered through a pad of silica
  6. washeluted with mixed solvent of EtOAc and Hexane (1:1)
  7. customThe crude product that obtained by removal of the solvent in vacuo
  8. customwas purified by flash column chromatography (10% EtOAc in hexane, Rf=0.20)

Sources & evidence

ORD record
ord-2a4d6aeb2dee4da4b2bc0fe64d650c46
Source dataset
uspto-grants-2012_05
Patent number
US08168635B2

Reaction notes

Loading…