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

HRID 1393655Notes

Reaction equation

HRID 1393655 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(#N)C>[CH3:12][N:13]([CH:15]=[C:2]([C:3]([CH3:5])=[O:4])[C:1]([O:7][CH2:8][CH3:9])=[O:6])[CH3:14]

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 3806790Ethyl 2-acetyl-3-(dimethylamino)acrylateYield 104.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl acetoacetate (35.4 g) was dissolved in acetonitrile (200 ml), and dimethylformamide dimethyl acetal (30.9 g) was added thereto, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure to give ethyl 2-dimethylaminomethyleneacetoacetate (50.4 g, Y.:99%) as a red oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-da8079a30519471bbc50995c291dc866
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

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