(E)-3-(4-benzyloxy-3,5-difluoro-phenyl)-acrylic acid ethyl ester → Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate

HRID 62836Notes

Reaction equation

HRID 62836 reaction equation
[CH2:1]([O:3][C:4](=[O:23])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[C:11]([F:13])[C:10]([O:14]CC2C=CC=CC=2)=[C:9]([F:22])[CH:8]=1)[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([OH:14])=[C:9]([F:22])[CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 90118234(E)-3-(4-benzyloxy-3,5-difluoro-phenyl)-acrylic acid ethyl ester

Product 1

HCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoateYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(E)-3-(4-Benzyloxy-3,5-difluoro-phenyl)-acrylic acid ethyl ester (1.2 g, 3.77 mmol) obtained in Step C was dissolved in EtOH (20 mL), and 10% Pd/C (120 mg) was added to the solution. The mixture was stirred at room temperature under hydrogen atmosphere for 12 hours. The reactant was filtered by using celite and concentrated under reduced pressure to obtain the title compound (0.85 g, 98%).

Workup

  1. filtrationThe reactant was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-04b6b1677efc443d9d11e4b92fcd26ee
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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