3-[3-(3-{3-[2,2,2-Trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-propoxy)-phenyl]-propionic acid ethyl ester → HCID 11584085, compound

HRID 1452690Notes

Reaction equation

HRID 1452690 reaction equation
[CH2:1]([O:3][C:4](=[O:43])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([O:33]CC3C=CC(OC)=CC=3)([C:29]([F:32])([F:31])[F:30])[C:25]([F:28])([F:27])[F:26])[CH:19]=2)[CH:8]=1)[CH3:2]>CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4](=[O:43])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([OH:33])([C:29]([F:31])([F:32])[F:30])[C:25]([F:26])([F:27])[F:28])[CH:19]=2)[CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 866042213-[3-(3-{3-[2,2,2-Trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-propoxy)-phenyl]-propionic acid ethyl ester

Product 1

HCID 11584085HCID 11584085, compoundYield 80.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

100 mg (0.16 mmol) of 3-[3-(3-{3-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-propoxy)-phenyl]-propionic acid ethyl ester in 10 mL of EtOAc were hydrogenated in the presence of 60 mg of 10% Pd/C. After removal of the catalyst and evaporation of the solvent, the residue was purified by column chromatography on silica gel with a gradient of EtOAc/n-heptane 1:5 to 1:3 to yield 64 mg (80%) of 3-(3-{3-[3-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-propoxy}-phenyl)-propionic acid ethyl ester as a colorless oil, MS: 493 (M−H)−.

Workup

  1. customAfter removal of the catalyst and evaporation of the solvent
  2. customthe residue was purified by column chromatography on silica gel with a gradient of EtOAc/n-heptane 1:5 to 1:3

Sources & evidence

ORD record
ord-74da447304bf4aeeabb9158407fdf30a
Source dataset
uspto-grants-2009_01
Patent number
US07473705B2

Reaction notes

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