Reaction #41144

ord-7ab93d08bb4a4e4f9f6760fb3038c041

Reaction equation

COC(=O)CC(C)=O
methyl acetoacetate
COC(OC)N(C)C
N,N-dimethylformamide dimethylacetal
→
COC(=O)C(=CN(C)C)C(C)=O
2-dimethylaminomethylene-3-oxo-butyric acid methyl ester
Yield 94.0%

Reactants

COC(=O)CC(C)=O
methyl acetoacetate
COC(OC)N(C)C
N,N-dimethylformamide dimethylacetal

Reagents

None

Conditions

Temperature
25°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Concentrationwas then concentrated in vacuo

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07728029B2uspto-grants-2010_06