Ethyl (2E)-4,4-difluoro-4-phenylbut-2-enoate → Ethyl 4,4-difluoro-4-phenylbutanoate

HRID 885535Notes

Reaction equation

HRID 885535 reaction equation
[F:1][C:2]([F:16])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)/[CH:3]=[CH:4]/[C:5]([O:7][CH2:8][CH3:9])=[O:6]>CO.[Pd]>[F:1][C:2]([F:16])([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 1

HCID 67244021Ethyl (2E)-4,4-difluoro-4-phenylbut-2-enoate

Product 1

HCID 67245996Ethyl 4,4-difluoro-4-phenylbutanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of Intermediate 20 (1 g, 4.42 mmol) in methanol (20 mL) was hydrogenated in the presence of palladium on charcoal (10 mg, 10%) for 3 hours. The mixture was then filtered over Celite and the solvent removed under reduced pressure. The residue (0.91 g) was used in the next step without further purification.

Workup

  1. filtrationThe mixture was then filtered over Celite
  2. customthe solvent removed under reduced pressure
  3. customThe residue (0.91 g) was used in the next step without further purification

Sources & evidence

ORD record
ord-bf2090b46cec44daaa7bca3f75165e98
Source dataset
uspto-grants-2012_08
Patent number
US08242177B2

Reaction notes

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