Ethyl 2-[5-benzyloxy-4'-(trifluoromethyl)biphenyl-3-yl]pentanoate → Ethyl 2-[5-hydroxy-4'-(trifluoromethyl)biphenyl-3-yl]pentanoate

HRID 226503Notes

Reaction equation

HRID 226503 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[CH:5]([C:9]1[CH:10]=[C:11]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[CH:12]=[C:13]([O:15]CC2C=CC=CC=2)[CH:14]=1)[CH2:6][CH2:7][CH3:8])[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:33])[CH:5]([C:9]1[CH:10]=[C:11]([C:23]2[CH:24]=[CH:25][C:26]([C:29]([F:31])([F:30])[F:32])=[CH:27][CH:28]=2)[CH:12]=[C:13]([OH:15])[CH:14]=1)[CH2:6][CH2:7][CH3:8])[CH3:2]

Participants

4

Reactant 1

HCID 24771799Ethyl 2-[5-benzyloxy-4'-(trifluoromethyl)biphenyl-3-yl]pentanoate

Product 1

HCID 24771789Ethyl 2-[5-hydroxy-4'-(trifluoromethyl)biphenyl-3-yl]pentanoateYield 96.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(5-Benzyloxy-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester (1.1 g, 2.4 mmol) was dissolved in EtOH (10 mL) and stirred with 10% Pd/C (116 mg) under an atmosphere of hydrogen. After 19 h, the mixture was filtered through Celite and concentrated in vacuo to afford 2-(5-hydroxy-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester (0.85 g) as a colourless oil.

Workup

  1. filtrationthe mixture was filtered through Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-51f41b0ab26148ada6848ca17f2ac712
Source dataset
uspto-grants-2009_07
Patent number
US07557244B2

Reaction notes

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