ethyl (4E)-5-(2-pyridyl)-4-pentenoate → Ethyl 5-(pyridin-2-yl)pentanoate

HRID 1741821Notes

Reaction equation

HRID 1741821 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)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

4

Reactant 1

HCID 11217977ethyl (4E)-5-(2-pyridyl)-4-pentenoate

Product 1

HCID 11241218Ethyl 5-(pyridin-2-yl)pentanoateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl (4E)-5-(2-pyridyl)-4-pentenoate (1.84 g) in ethanol (15 ml) was added 10% palladium on carbon (145 mg), and the mixture was stirred for 3 hours under an atmosphere of hydrogen (4 atm), and then filtered through a celite pad. Removal of the solvent in vacuo gave ethyl 5-(2-pyridyl)pentanoate (1.84 g).

Workup

  1. filtrationfiltered through a celite pad
  2. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-311dbe55b5d645dd9b512fd76a1be2f3
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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