Ammonium formate → Ethyl 5-(pyridin-2-yl)pentanoate

HRID 748394Notes

Reaction equation

HRID 748394 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[CH:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C([O-])=O.[NH4+]>C(O)C.O.[C].[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 54207534Ethyl 5-(2-pyridyl)-4-pentenoate

Product 1

HCID 11241218Ethyl 5-(pyridin-2-yl)pentanoateYield 94.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 5-(2-pyridyl)-4-pentenoate (1.7 g, 8.2 mmol) was dissolved in ethanol (20 ml), and 10% palladium-carbon (0.22 g) and a solution of ammonium formate (3.1 g, 49.0 mmol) in water (5 ml) were added thereto. The reaction mixture was refluxed for 2 hrs. Palladium-carbon was filtered off, and the reaction mixture was combined with ethyl acetate and water. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the titled compound (1.6 g, 94%).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hrs
  2. filtrationPalladium-carbon was filtered off
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-12483f08868948e795205bff731d6937
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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