HCID 68867447, compound → HCID 68869672, compound

HRID 1985256Notes

Reaction equation

HRID 1985256 reaction equation
[CH:1]1([O:6][C:7](=[O:30])[CH:8]([O:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16]CC3C=CC=CC=3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>CCOC(C)=O.[Pd]>[CH:1]1([O:6][C:7](=[O:30])[CH:8]([O:24][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)[CH2:9][C:10]2[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 68867447HCID 68867447, compound

Product 1

HCID 68869672HCID 68869672, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(4-benzyloxy-phenyl)-2-cyclopentyloxy-propionic acid cyclopentyl ester (0.137 g, 0.335 mmol) and 10% Pd/C (0.14 g) in EtOAc (70 mL) was purged with N2 then H2 and then stirred under a H2 balloon atmosphere for 3 h at room temperature. Upon reaction completion, MgSO4 was added and the mixture filtered through hyflo. The solvent was removed in vacuo to afford 0.090 g (84%) 2-cyclopentyloxy-3-(4-hydroxy-phenyl)-propionic acid cyclopentyl ester. 1H NMR. MS (ES−) Calc'd for C19H25O4 (M−1) 317. Found m/z 317 (100%).

Workup

  1. customwas purged with N2
  2. customUpon reaction completion, MgSO4
  3. additionwas added
  4. filtrationthe mixture filtered through hyflo
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e6b3638f2b834030b9c17ef197286d91
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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