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

HRID 499576Notes

Reaction equation

HRID 499576 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-bd38c9a6c3194cda84d8aa360828a886
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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