Ethyl-3-(5'-fluoro-2'-methoxybenzyl)acrylate → Ethyl-4-(5'-fluoro-2'-methoxyphenyl)butyrate

HRID 1919518Notes

Reaction equation

HRID 1919518 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]=[CH:6][CH2:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])[CH3:2]

Participants

4

Reactant 1

HCID 67499893Ethyl-3-(5'-fluoro-2'-methoxybenzyl)acrylate

Product 1

HCID 67499284Ethyl-4-(5'-fluoro-2'-methoxyphenyl)butyrateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl-3-(5′-fluoro-2′-methoxybenzyl)acrylate (2.36 g, 10.0 mmol) in ethanol (100%, 40 mL) under Ar(g) was added Pd/C (10%, 200 mg) very carefully and the flask containing the mixture was evacuated and purged with H2 three time each. Then a balloon was attached to the flask and the reaction was allowed to go for 15 h at room temperature. 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 a flash column chromatography (10% EtOAc in hexane, Rf=0.20) to give the product (2.25 g, 95%).

Workup

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

Sources & evidence

ORD record
ord-be14934034144929a1b44daa136a13e2
Source dataset
uspto-grants-2012_05
Patent number
US08168635B2

Reaction notes

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