Benzyl 2-(3-fluoro-4-((2-methoxyethoxy)methyl)phenyl)acrylate → 2-(3-Fluoro-4-((2-methoxyethoxy)methyl)phenyl)propanoic acid

HRID 1842923Notes

Reaction equation

HRID 1842923 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:14](=[CH2:25])[C:15]([O:17]CC2C=CC=CC=2)=[O:16])[CH:5]=[CH:6][C:7]=1[CH2:8][O:9][CH2:10][CH2:11][O:12][CH3:13]>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:25])[C:15]([OH:17])=[O:16])[CH:5]=[CH:6][C:7]=1[CH2:8][O:9][CH2:10][CH2:11][O:12][CH3:13]

Participants

4

Reactant 1

HCID 59637287Benzyl 2-(3-fluoro-4-((2-methoxyethoxy)methyl)phenyl)acrylate

Product 1

HCID 596372702-(3-Fluoro-4-((2-methoxyethoxy)methyl)phenyl)propanoic acidYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of benzyl 2-(3-fluoro-4-((2-methoxyethoxy)methyl)phenyl)acrylate (2.8 g, 8.139 mmol), 10% Pd/C (300 mg) in MeOH (20 mL) was hydrogenated (balloon pressure) at RT for 1 h until complete consumption of benzyl 2-(3-fluoro-4-((2-methoxyethoxy)methyl)phenyl)acrylate, as evidenced by TLC analysis. The reaction mixture was filtered through celite pad, washed with MeOH (2×15 mL). The combined filtrate was concentrated and the obtained crude compound was purified by CC using 30% EtOAc in PE as eluent to afford 2-(3-fluoro-4-((2-methoxyethoxy)methyl)phenyl)propanoic acid (1.2 g, 58%) as a colorless oil (TLC solvent system: 30% EtOAc-PE; Rf: 0.15).

Workup

  1. customat RT
  2. customfor 1 h
  3. customuntil complete consumption of benzyl 2-(3-fluoro-4-((2-methoxyethoxy)methyl)phenyl)acrylate
  4. filtrationThe reaction mixture was filtered through celite pad
  5. washwashed with MeOH (2×15 mL)
  6. concentrationThe combined filtrate was concentrated
  7. customthe obtained crude compound
  8. customwas purified by CC

Sources & evidence

ORD record
ord-4958adbc1da94478a799fe6da0570db6
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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