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

HRID 604299Notes

Reaction equation

HRID 604299 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].CO[CH:12]([N:15]([CH3:17])[CH3:16])OC>>[CH2:8]([O:7][C:1](=[O:6])[C:2](=[CH:12][N:15]([CH3:17])[CH3:16])[C:3](=[O:4])[CH3:5])[CH3:9]

Participants

3

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 3806790Ethyl 2-acetyl-3-(dimethylamino)acrylateYield 99.3%

Procedure

Add ethyl acetoacetate (15 mL, 0.118 mol) to dimethoxymethyl-dimethyl-amine (19 mL, 0.142 mol) and reflux the mixture for 1 hr. Evaporate the mixture to give 2-dimethylaminomethylene-3-oxo-butyric acid ethyl ester (21.7 g, 99%).

Workup

  1. temperaturereflux the mixture for 1 hr
  2. customEvaporate the mixture

Sources & evidence

ORD record
ord-2dc63bbebc7e408fb93b63af1b12f01c
Source dataset
uspto-grants-2011_03
Patent number
US07910588B2

Reaction notes

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