3-(4-Benzyloxy-phenyl)-2-(2-methoxy-phenoxy)-2-methyl-3-(2,2,2-trifluoro-acetoxy)-propionic acid ethyl ester → 3-(4-Hydroxyphenyl)-2-(2-methoxy-phenoxy)-2-methyl-propionic acid ethyl ester

HRID 348380Notes

Reaction equation

HRID 348380 reaction equation
[CH2:1]([O:3][C:4](=[O:38])[C:5]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36][CH3:37])([CH3:28])[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:38])[C:5]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36][CH3:37])([CH3:28])[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 693542413-(4-Benzyloxy-phenyl)-2-(2-methoxy-phenoxy)-2-methyl-3-(2,2,2-trifluoro-acetoxy)-propionic acid ethyl ester

Product 1

HCID 588018243-(4-Hydroxyphenyl)-2-(2-methoxy-phenoxy)-2-methyl-propionic acid ethyl esterYield 25%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-(4-Benzyloxy-phenyl)-2-(2-methoxy-phenoxy)-2-methyl-3-(2,2,2-trifluoro-acetoxy)-propionic acid ethyl ester was dissolved in ethyl acetate (350 mL), treated with 5% palladium on carbon (8.77 g), and stirred under an atmosphere of hydrogen for 48 h. The suspension was filtered through celite and concentrated in vacuo. The residue was purified by flash column chromatography (25% ethyl acetate in hexanes) to provide the title compound as a light yellow oil (1.73 g, 25%). 1H NMR (400 MHz, CDCl3): δ 7.12 (d, 2H, J=6.65 Hz), 6.98–6.93 (m, 5H), 4.24–4.15 (m, 2H), 3.75 (s, 3H), 3.23 (d; 1H, J=13.69 Hz), 3.13 (d, 1H, J=13.69 Hz), 1.30 (s, 3H), 1.22 (t, 3H, J=7.43 Hz). MS [EI+] 331 (M+H)+, [EI−] 329 (M−H)+. Rf=0.14 in 25% ethyl acetate in hexanes.

Workup

  1. filtrationThe suspension was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash column chromatography (25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0b29e708cd644dbda4e3ba0946de5de0
Source dataset
uspto-grants-2007_02
Patent number
US07176224B2

Reaction notes

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