Ethyl 3-methyl-3-pyridin-4-ylprop-2-enoate → Ethyl 3-(pyridin-4-yl)butanoate

HRID 1064022Notes

Reaction equation

HRID 1064022 reaction equation
[CH3:1][C:2]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]>C(O)C.[Pd]>[CH3:1][CH:2]([C:9]1[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 1

HCID 69315756Ethyl 3-methyl-3-pyridin-4-ylprop-2-enoate

Product 1

HCID 22277801Ethyl 3-(pyridin-4-yl)butanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 3-methyl-3-pyridin-4-ylprop-2-enoate (Method 9; 8.4 g, 44 mmol) in ethanol (150 ml) was added 5% palladium on charcoal. The mixture was stirred under an atmosphere of hydrogen for 18 hours. The mixture was filtered through diatomaceous earth and the filtrate evaporated to leave a colourless oil. The crude product was purified by chromatography eluting with 30-50% EtOAc in hexane to give the product as a colourless oil. M/z 194.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. customthe filtrate evaporated
  3. customto leave a colourless oil
  4. customThe crude product was purified by chromatography
  5. washeluting with 30-50% EtOAc in hexane

Sources & evidence

ORD record
ord-93d2f764bfec41f098ff46641a11cb07
Source dataset
uspto-grants-2005_11
Patent number
US06967216B2

Reaction notes

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