HCID 69073335, compound → HCID 57894203, compound

HRID 1822314Notes

Reaction equation

HRID 1822314 reaction equation
[CH2:1]([O:3][C:4](=[O:42])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([O:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=3[O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[CH3:38])[CH:17]=[C:16]([CH3:39])[CH:15]=2)=[CH:9][C:8]=1[CH2:40][CH3:41])[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:42])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([O:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:29])([F:30])[F:28])=[CH:23][C:22]=3[O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[CH3:38])[CH:17]=[C:16]([CH3:39])[CH:15]=2)=[CH:9][C:8]=1[CH2:40][CH3:41])[CH3:2]

Participants

4

Reactant 1

HCID 69073335HCID 69073335, compound

Product 1

HCID 57894203HCID 57894203, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-{2-ethyl-4-[3-methyl-5-(2-o-tolyloxy-4-trifluoromethyl-phenoxy)phenoxy]-phenyl}-acrylic acid ethyl ester (1.83 g, 3.17 mmol) and 10% Pd/C (1.80 g) in ethyl acetate (100 mL) is purged with N2 then H2 and then stirred under a H2 balloon at rt for 5 hours. The mixture is filtered through hyflo, and the solvent is removed in vacuo to afford 1.77 g (97%) of the title compound. Rf=0.22 (9/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calculated for C34H33F3O5 578, found 579 (M+1, 100%).

Workup

  1. customis purged with N2
  2. filtrationThe mixture is filtered through hyflo
  3. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-81a46ffd75e54bfda8fbb9b2fbc2a75f
Source dataset
uspto-grants-2009_10
Patent number
US07608639B2

Reaction notes

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