[(2-Methyl-4-{2-[4'-(trifluoromethyl)-3-biphenylyl]ethenyl}phenyl)oxy]acetic acid → [(2-Methyl-4-{2-[4'-(trifluoromethyl)-3-biphenylyl]ethyl}phenyl)oxy]acetic acid

HRID 1391804Notes

Reaction equation

HRID 1391804 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH:8]=[CH:9][C:10]2[CH:11]=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[O:26][CH2:27][C:28]([OH:30])=[O:29]>CCO.[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[O:26][CH2:27][C:28]([OH:30])=[O:29]

Participants

4

Reactant 1

HCID 69210988[(2-Methyl-4-{2-[4'-(trifluoromethyl)-3-biphenylyl]ethenyl}phenyl)oxy]acetic acid

Product 1

HCID 10024789[(2-Methyl-4-{2-[4'-(trifluoromethyl)-3-biphenylyl]ethyl}phenyl)oxy]acetic acidYield 109.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of [(2-methyl-4-{2-[4′-(trifluoromethyl)-3-biphenylyl]ethenyl}phenyl)oxy]acetic acid (90 mg, 0.22 mmol) in EtOH (10 mL) was added to Pd/C (Degussa type E101 NE/N) (10 mg, 11 wt %) and the resulting mixture stirred under an atmosphere of hydrogen for 6 hours. The mixture was then filtered through celite J2 washing with copious amounts of EtOH and the filtrate reduced under vacuum to give a sticky solid (100 mg) which was purified by mass directed auto-prep HPLC to give the title compound as a fluffy white solid (25 mg).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. washJ2 washing with copious amounts of EtOH

Sources & evidence

ORD record
ord-863d83558f074fdbb9de805408ad7720
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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