ethyl (2Z)-3-(pyridin-4-yl)but-2-enoate → Ethyl 3-(pyridin-4-yl)butanoate

HRID 1896255Notes

Reaction equation

HRID 1896255 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](/[C:7](/[CH3:14])=[CH:8]\[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:3][CH:2]=1>[Pd].CCO>[N:1]1[CH:6]=[CH:5][C:4]([CH:7]([CH3:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 69315754ethyl (2Z)-3-(pyridin-4-yl)but-2-enoate

Product 1

HCID 22277801Ethyl 3-(pyridin-4-yl)butanoateYield 71.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium on carbon (70 mg, 10 wt. %) was added to a solution of (Z)-ethyl 3-(pyridin-4-yl)but-2-enoate (0.70 g, 3.66 mmol) in EtOH (10 ml) and hydrogenated under balloon pressure for 18 h. The reaction mixture was filtered through a pad of celite and washed with EtOH. The filtrate was concentrated under reduced pressure to afford 0.50 g (71.4%) of ethyl 3-(pyridin-4-yl)butanoate as light brown color liquid.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washwashed with EtOH
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4e5b3642c0874bbf869a6e1cc5ad1df8
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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