3-(4-Benzyloxy-phenyl)-2-methyl-2-o-tolyloxy-3-(2,2,2-trifluoro-acetoxy)-propionic acid ethyl ester → 3-(4-Hydroxy-phenyl)-2-methyl-2-o-tolyloxypropionic acid ethyl ester

HRID 1393491Notes

Reaction equation

HRID 1393491 reaction equation
[CH2:1]([O:3][C:4](=[O:37])[C:5]([CH3:36])([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH3:35])[CH:6]([C:14]1[CH:19]=[CH:18][C:17]([O:20]CC2C=CC=CC=2)=[CH:16][CH:15]=1)OC(=O)C(F)(F)F)[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:37])[C:5]([CH3:36])([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH3:35])[CH2:6][C:14]1[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=1)[CH3:2]

Participants

4

Reactant 1

HCID 208231483-(4-Benzyloxy-phenyl)-2-methyl-2-o-tolyloxy-3-(2,2,2-trifluoro-acetoxy)-propionic acid ethyl ester

Product 1

HCID 208231553-(4-Hydroxy-phenyl)-2-methyl-2-o-tolyloxypropionic acid ethyl esterYield 106.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-(4-Benzyloxy-phenyl)-2-methyl-2-o-tolyloxy-3-(2,2,2-trifluoro-acetoxy)-propionic acid ethyl ester (7.4 g, 14.3 mmol) was dissolved in ethyl acetate (300 mL), treated with 5% palladium on carbon (7.4 g), and stirred under an atmosphere of hydrogen for 96 h. The suspension was filtered through celite and concentrated in vacuo to provide the titled compound (4.8 g, 100%) as an opaque yellow oil.

Workup

  1. filtrationThe suspension was filtered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a9eea499c96043a295c2d91129ef9eee
Source dataset
uspto-grants-2008_03
Patent number
US07345070B2

Reaction notes

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