Ethyl 3-{3,5-difluoro-2-[2-(ethoxycarbonyl)vinyl]phenyl}acrylate → Ethyl 3-{3,5-difluoro-2-[2-(ethoxycarbonyl)ethyl]phenyl}propionate

HRID 863060Notes

Reaction equation

HRID 863060 reaction equation
[F:1][C:2]1[C:3]([CH:16]=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:4]([CH:9]=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[C:3]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:4]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 1

HCID 53722136Ethyl 3-{3,5-difluoro-2-[2-(ethoxycarbonyl)vinyl]phenyl}acrylate

Product 1

HCID 19699411Ethyl 3-{3,5-difluoro-2-[2-(ethoxycarbonyl)ethyl]phenyl}propionateYield 121.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 3-{3,5-difluoro-2-[2-(ethoxycarbonyl)vinyl]phenyl}acrylate (5.7 g, 18.4 mmol) in 250 mL of ethyl acetate was hydrogenated at 60 psi over 10% palladium on carbon (0.57 g) for 4 hours and then the mixture was filtered through Celite. Evaporation of the solvent gave ethyl 3-{3,5-difluoro-2-[2-(ethoxycarbonyl)ethyl]phenyl}propionate (5.73 g, 22.4 mmol) as a colorless oil.

Workup

  1. filtrationthe mixture was filtered through Celite
  2. customEvaporation of the solvent

Sources & evidence

ORD record
ord-98a402fe569f4c5eb6bc2e0ac3e25fd9
Source dataset
uspto-grants-1998_02
Patent number
US05719280

Reaction notes

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