4-Methyl-3-(2-pyridyl)phenyl-pent-4-enoic acid → 4-Methyl-3-(2-pyridyl)phenyl-valeric acid

HRID 1058588Notes

Reaction equation

HRID 1058588 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][CH:13]=[CH2:14])[C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.[H][H]>CCO.Cl.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][CH2:13][CH3:14])[C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1

Participants

6

Reactant 2

HCID 698427514-Methyl-3-(2-pyridyl)phenyl-pent-4-enoic acidHCID 178418361HCID 178418361, compound2×

Product 1

HCID 698426234-Methyl-3-(2-pyridyl)phenyl-valeric acidYield 60%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 313Hydrochloric AcidSolvent2×HCID 702EthanolSolvent

Procedure

4-Methyl-3-(2-pyridyl)phenyl-pent-4-enoic acid (0.5 g, 1.87 mmol) was dissolved in EtOH (15 ml) and 6N HCl (0.15 ml). 10% Palladium on carbon (0.08 g) was added and the reaction mixture was stirred under a balloon of hydrogen gas overnight. Then, additional 10% palladium on carbon (0.09 g) and 6N HCl (0.2 ml) were added and the reaction was stirred under a balloon of hydrogen gas for an additional 6 h. The reaction mixture was then filtered through a pad of Celite, azeotroped with toluene (40 ml) and was suspended in water (3 ml). Aqueous sodium hydroxide (1 M) was then added dropwise until the pH was adjusted to 7. The aqueous layer was then extracted with chloroform 2 times and the combined organics were dried with magnesium sulfate, concentrated in vacuo, and triturated with hexanes/Et2O to yield a white solid (0.3 g, 60%): MS ES(+) 270.1 (M+H+).

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of Celite
  2. customazeotroped with toluene (40 ml)
  3. additionAqueous sodium hydroxide (1 M) was then added dropwise until the pH
  4. extractionThe aqueous layer was then extracted with chloroform 2 times
  5. dry with materialthe combined organics were dried with magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customtriturated with hexanes/Et2O

Sources & evidence

ORD record
ord-8303b8f7f43944fc8a0339b0485bc6ff
Source dataset
uspto-grants-2003_02
Patent number
US06518267B1

Reaction notes

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