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

HRID 1044734Notes

Reaction equation

HRID 1044734 reaction equation
N#N.CC[O-].[Na+].[C:7]([O:13][CH2:14][CH3:15])(=[O:12])[CH2:8][C:9]([CH3:11])=[O:10].[C:16](#[N:19])[CH:17]=[CH2:18]>>[CH2:14]([O:13][C:7](=[O:12])[CH:8]([C:9](=[O:10])[CH3:11])[CH2:18][CH2:17][C:16]#[N:19])[CH3:15]

Participants

5

Reactant 4

HCID 947NitrogenHCID 7855AcrylonitrileHCID 8868Ethyl AcetoacetateHCID 2723922Sodium ethoxide

Product 1

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

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to sodium ethylate (prepared from 62 mg sodium in 8 mL of EtOH) was added ethyl acetoacetate (9.7 mL, 76.1 mmol). Acrylonitrile (5 mL, 76.1 mmol) was then added dropwise at 40-45° C. and the reaction mixture was stirred at this temperature overnight. Ethanol was removed and the residue washed with 65 mL of water containing 3.5 mL of acetic acid, diluted with CH2Cl2 and dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was distilled (bp=95-105° C. at 1 atm) to give the title compound. TLC:rf (7:3 hept-EA)=0.29.

Workup

  1. customEthanol was removed
  2. washthe residue washed with 65 mL of water containing 3.5 mL of acetic acid
  3. additiondiluted with CH2Cl2
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. distillationThe crude residue was distilled (bp=95-105° C. at 1 atm)

Sources & evidence

ORD record
ord-558c5b562031494897346cb06ae86c78
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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