Methyl 3-(3-(benzyloxy)-5-fluorophenyl)acrylate → Methyl 3-(3-fluoro-5-hydroxyphenyl)propanoate

HRID 709682Notes

Reaction equation

HRID 709682 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]([O:20][CH3:21])=[O:19])[CH:12]=[C:13]([F:15])[CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[F:15][C:13]1[CH:12]=[C:11]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:10]=[C:9]([OH:8])[CH:14]=1

Participants

4

Reactant 1

HCID 131733901Methyl 3-(3-(benzyloxy)-5-fluorophenyl)acrylate

Product 1

HCID 91618985Methyl 3-(3-fluoro-5-hydroxyphenyl)propanoateYield 39.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(3-(benzyloxy)-5-fluorophenyl)acrylate (2.60 g) in methanol (15 mL) was added 10% palladium-activated carbon (2.20 g), and the mixture was stirred for 1 hr under a hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (710 mg) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5d39305c6f51429d94645ec22a78936f
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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