Acrylonitrile → Ethyl 2-(2-cyanoethyl)-3-oxobutanoate

HRID 1807485Notes

Reaction equation

HRID 1807485 reaction equation
[Na].[C:2]([O:8][CH2:9][CH3:10])(=[O:7])[CH2:3][C:4]([CH3:6])=[O:5].[C:11](#[N:14])[CH:12]=[CH2:13]>CCO>[C:11]([CH2:12][CH2:13][CH:3]([C:4](=[O:5])[CH3:6])[C:2]([O:8][CH2:9][CH3:10])=[O:7])#[N:14]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 8868Ethyl AcetoacetateHCID 5360545Sodium

Product 1

HCID 13328085Ethyl 2-(2-cyanoethyl)-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of solid sodium metal (450 mg, 19.75 mmol) in EtOH at 30° C. was treated with ethyl acetoacetate (103 g, 790 mmol) maintaining temperature. Then acrylonitrile (41.9 g, 790 mmol) was added dropwise over 15 minutes. The reaction was capped and stirred for 4 hours. The solution was concentrated and the resulting solid was dissolved in 20 mL of water and 3 mL of acetic acid, and washed with 50 mL of DCM. The organic layer was dried over Na2SO4 and concentrated to an oil. Distillation was performed under reduced pressure (0.5 mm) with a bath temperature of 80° C. Fractions were collected and concentrated to provide A-1 as a colorless oil. Data for A-1: LC/MS: m/z (M+H)=183.87 found; 183.20 required

Workup

  1. temperaturemaintaining temperature
  2. customThe reaction was capped
  3. concentrationThe solution was concentrated
  4. dissolutionthe resulting solid was dissolved in 20 mL of water
  5. wash3 mL of acetic acid, and washed with 50 mL of DCM
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated to an oil
  8. distillationDistillation
  9. customwas performed under reduced pressure (0.5 mm) with a bath
  10. customtemperature of 80° C
  11. customFractions were collected
  12. concentrationconcentrated
  13. customto provide A-1 as a colorless oil

Sources & evidence

ORD record
ord-bb63ec3371ff44028b1d6ad25fc9eb47
Source dataset
uspto-grants-2013_01
Patent number
US08357700B2

Reaction notes

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