HCID 57894198, compound → HCID 57894137, compound

HRID 1822353Notes

Reaction equation

HRID 1822353 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19]CC3C=CC=CC=3)[CH:14]=2)=[CH:8][C:7]=1[CH3:27]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)=[CH:8][C:7]=1[CH3:27]

Participants

4

Reactant 1

HCID 57894198HCID 57894198, compound

Product 1

HCID 57894137HCID 57894137, compoundYield 102%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-[4-(3-benzyloxy-phenoxy)-2-methyl-phenyl]-propionic acid methyl ester (10.54 g, 28.0 mmol) and 10% Pd/C (5 g) in ethyl acetate (150 mL) is purged with N2, and then purged with H2, which is stirred under a hydrogen balloon. Upon reaction completion, the mixture is filtered through Hyflo, and the solvent is removed in vacuo to afford about 8.18 g (100%) of the titled compound. Rf=0.59 (4/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calcd for C17H18O4 286, found 287 (M+1, 100%).

Workup

  1. customis purged with N2
  2. custompurged with H2, which
  3. customUpon reaction completion
  4. filtrationthe mixture is filtered through Hyflo
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-1d38185648394dbe95620bdafae9ed65
Source dataset
uspto-grants-2009_10
Patent number
US07608639B2

Reaction notes

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