(Z)-ethyl 3-(4-(benzyloxy)-3,5-difluorophenyl)-2-ethoxyacrylate → Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)-2-ethoxypropanoate

HRID 1876412Notes

Reaction equation

HRID 1876412 reaction equation
C([O:8][C:9]1[C:14]([F:15])=[CH:13][C:12](/[CH:16]=[C:17](\[O:23][CH2:24][CH3:25])/[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:11][C:10]=1[F:26])C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[F:15][C:14]1[CH:13]=[C:12]([CH2:16][CH:17]([O:23][CH2:24][CH3:25])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:11]=[C:10]([F:26])[C:9]=1[OH:8]

Participants

5

Reactant 2

HCID 59419855(Z)-ethyl 3-(4-(benzyloxy)-3,5-difluorophenyl)-2-ethoxyacrylateHCID 178418361HCID 178418361, compound

Product 1

HCID 59419836Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)-2-ethoxypropanoateYield 82.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution (Z)-ethyl 3-(4-(benzyloxy)-3,5-difluorophenyl)-2-ethoxyacrylate (680) (1.3 g, 3.59 mmol) in ethanol (25 mL) was added Pd/C (140 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 overnight at room temperature, was filtered through a pad of celite and concentrated in vacuo to give ethyl 3-(3,5-difluoro-4-hydroxyphenyl)-2-ethoxypropanoate (0.81 g) (681).

Workup

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

Sources & evidence

ORD record
ord-f42e5f22046840e3bf7f86497ec62c1a
Source dataset
uspto-grants-2012_11
Patent number
US08309600B2

Reaction notes

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