ethyl (2E)-3-(3,5-difluoro-4-hydroxyphenyl)prop-2-enoate → Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate

HRID 1909512Notes

Reaction equation

HRID 1909512 reaction equation
[F:1][C:2]1[CH:3]=[C:4](/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[C:6]([F:9])[C:7]=1[OH:8].[H][H]>C(O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[C:6]([F:9])[C:7]=1[OH:8]

Participants

5

Reactant 2

HCID 59419838ethyl (2E)-3-(3,5-difluoro-4-hydroxyphenyl)prop-2-enoateHCID 178418361HCID 178418361, compound

Product 1

HCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (E)-ethyl 3-(3,5-difluoro-4-hydroxyphenyl)acrylate (10) (0.751 g, 3.29 mmol) in ethanol (20 mL) was added Pd/C (81 mg, 10% Degussa type). A balloon of hydrogen gas was added and the reaction was evacuated and back-filled with hydrogen three times. The reaction was stirred under a hydrogen balloon overnight at room temperature, filtered through a pad of celite and concentrated in vacuo to give ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate (11).

Workup

  1. customthe reaction was evacuated
  2. additionback-filled with hydrogen three times
  3. filtrationfiltered through a pad of celite
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-076f931b7b91495baa864d8135781fc2
Source dataset
uspto-grants-2013_12
Patent number
US08598374B2

Reaction notes

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