Methyl acetoacetate → Methyl 2-((dimethylamino)methylene)-3-oxobutanoate

HRID 12866

Reaction equation

HRID 12866 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].CO[CH:11](OC)[N:12]([CH3:14])[CH3:13]>>[CH3:8][O:7][C:1](=[O:6])[C:2](=[CH:11][N:12]([CH3:14])[CH3:13])[C:3](=[O:4])[CH3:5]

Participants

3

Reactant 2

HCID 7757Methyl acetoacetateHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 53395488Methyl 2-((dimethylamino)methylene)-3-oxobutanoateYield 94%

Conditions

Temperature
25 °C

Procedure

A solution of methyl acetoacetate (5.0 mL, 46.33 mmol) and N,N-dimethylformamide dimethylacetal (6.8 mL, 47.95 mmol) was heated to 80° C. for 2.3 h. At this time, the reaction was cooled to 25° C. and was then concentrated in vacuo to afford 2-dimethylaminomethylene-3-oxo-butyric acid methyl ester (7.43 g, 94%) as a red/black solid. This material was used without further purification.

Workup

  1. concentrationwas then concentrated in vacuo

Sources & evidence

ORD record
ord-7ab93d08bb4a4e4f9f6760fb3038c041
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Linked notes

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