2-Biphenyl-3-yl-4-methylpent-4-enoic acid → 2-Biphenyl-3-yl-4-methylpentanoic acid

HRID 1060737

Reaction equation

HRID 1060737 reaction equation
[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([CH2:11][C:12]([CH3:14])=[CH2:13])[C:8]([OH:10])=[O:9])[CH:2]=1>C(O)C.[Pd]>[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:8]([OH:10])=[O:9])[CH:2]=1

Participants

4

Reactant 1

HCID 218997992-Biphenyl-3-yl-4-methylpent-4-enoic acid

Product 1

HCID 218997772-Biphenyl-3-yl-4-methylpentanoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-biphenyl-3-yl-4-methylpent-4-enoic acid (250 mg, 0.9 mmol), prepared as in Example 2, and 5% Pd/C (50 mg) in 10 ml of ethanol was hydrogenated (40 psi) for 2 hours. The mixture was filtered and the filtrate concentrated to provide 2-biphenyl-3-yl-4-methylpentanoic acid (250 mg, 0.9 mmol). 1H NMR (DMSO-d6): 1.01 (d, 6H), 1.81-1.85 (m, 3H), 3.68 (dd, 1H), 7.08 (d, 1H), 7.24-7.37 (m, 8H). LCMS: 269.1 (M+H+).

Workup

  1. customfor 2 hours
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-d08b3ca76b934058a98d363d330a0973
Source dataset
uspto-grants-2003_02
Patent number
US06525036B2

Linked notes

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