Ethyl Acetate → 3-Pyridin-2-yl-propionic acid tert-butyl ester

HRID 499329Notes

Reaction equation

HRID 499329 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1/[CH:7]=[CH:8]/[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C([O-])=O.[NH4+].C(OCC)(=O)C>C(O)C.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 2723923Ammonium formateHCID 10899753(E)-tert-Butyl 3-(pyridin-2-yl)acrylate

Product 1

HCID 591086993-Pyridin-2-yl-propionic acid tert-butyl esterYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

tert-Butyl (E)-3-(2-pyridyl)-2-propenoate (1.1 g, 5.4 mmol) was dissolved in ethanol (12 ml), and a solution of ammonium formate (2.0 g, 32.0 mmol) in water (3 ml) was added thereto. The reaction mixture was refluxed for 1.5 hrs, combined with ethyl acetate and water and filtered. The filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the titled compound (1.0 g, 94%).

Workup

  1. temperatureThe reaction mixture was refluxed for 1.5 hrs
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e48904e737614a75a56e9a05c8703193
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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