Ethyl Acetoacetate → Ethyl 2-acetyl-3-(dimethylamino)acrylate

HRID 388820Notes

Reaction equation

HRID 388820 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].CO[CH:12](OC)[N:13]([CH3:15])[CH3:14]>>[CH3:12][N:13]([CH:15]=[C:2]([C:3](=[O:4])[CH3:5])[C:1]([O:7][CH2:8][CH3:9])=[O:6])[CH3:14]

Participants

3

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 3806790Ethyl 2-acetyl-3-(dimethylamino)acrylateYield 93.9%

Procedure

Ethyl acetoacetate (15 g, 115 mmol) and N,N-Dimethylformamide dimethyl Acetal (13.7 g, 115 mmol) stirred at rt for overnight. After completion of the reaction, reaction mixture distilled on rotavapour to obtain the crude. Crude was purified by column chromatography over 60-120 mesh silica gel using EtOAc and petether (10:90) as eluent to obtain the title compound (20 g).

Workup

  1. customAfter completion of the reaction, reaction mixture
  2. distillationdistilled on rotavapour
  3. customto obtain the crude
  4. customCrude was purified by column chromatography over 60-120 mesh silica gel

Sources & evidence

ORD record
ord-40b42a7bd91b4d09b35eb83c4958c7d2
Source dataset
uspto-grants-2013_02
Patent number
US08377970B2

Reaction notes

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