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

HRID 1268743Notes

Reaction equation

HRID 1268743 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]>>[C:3]([C:2](=[CH:12][N:13]([CH3:15])[CH3:14])[C:1]([O:7][CH2:8][CH3:9])=[O:6])(=[O:4])[CH3:5]

Participants

3

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 3806790Ethyl 2-acetyl-3-(dimethylamino)acrylateYield 74%

Procedure

Ethyl acetoacetate (79 mL, 0.62 mol) was added to N,N-dimethylformamide dimethylacetal (100 mL, 0.68 mol) and the mixture was heated under reflux for 1 hr. The excess amount of acetal was evaporated under reduced pressure and the residue was subjected to distillation under reduced pressure to give the title compound (85 g, yield 74%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. customThe excess amount of acetal was evaporated under reduced pressure
  4. distillationthe residue was subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-ead299a04e2142dd917635ad87a9dcb2
Source dataset
uspto-grants-2007_04
Patent number
US07199124B2

Reaction notes

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