Ammonium formate → tert-Butyl 3-(pyridin-4-yl)propanoate

HRID 748411Notes

Reaction equation

HRID 748411 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:3][CH:2]=1.C([O-])=O.[NH4+]>C(O)C.O.[C].[Pd]>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 11805847tert-Butyl (E)-3-(4-Pyridyl)acrylate

Product 1

HCID 14799559tert-Butyl 3-(pyridin-4-yl)propanoateYield 65.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

tert-Butyl (E)-3-(4-Pyridyl)acrylate (0.88 g, 4.3 mmol) was dissolved in ethanol (10 ml), and 10% palladium-carbon (0.17 g) and a solution of ammonium formate (1.4 g, 21.4 mmol) in water (2.5 ml) were added thereto. The reaction mixture was refluxed for 3 hrs. Palladium-carbon was filtered off. The reaction mixture was combined with water, concentrated under reduced pressure to the half amount and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel (20 g) column chromatography. The fractions eluted with hexane-ethyl acetate (3:1, v/v) were collected and concentrated to give the titled compound (0.58 g, 65%).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hrs
  2. filtrationPalladium-carbon was filtered off
  3. concentrationconcentrated under reduced pressure to the half amount
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated
  8. washThe fractions eluted with hexane-ethyl acetate (3:1
  9. customv/v) were collected
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-734f8a71c3ec4d9399b6fd45dd7f6ba8
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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