Ethyl 4,4,4-trifluoroacetoacetate → Butanoic acid, 2-[(dimethylamino)methylene]-4,4,4-trifluoro-3-oxo-, ethyl ester

HRID 1805273Notes

Reaction equation

HRID 1805273 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].CO[CH:15](OC)[N:16]([CH3:18])[CH3:17]>C1C=CC=CC=1>[CH3:15][N:16]([CH:18]=[C:4]([C:3](=[O:10])[C:2]([F:11])([F:12])[F:1])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:17]

Participants

4

Reactant 2

HCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 53979199Butanoic acid, 2-[(dimethylamino)methylene]-4,4,4-trifluoro-3-oxo-, ethyl esterYield 65%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Ethyl 4,4,4-trifluoroacetoacetate (18.5 g, 77.34 mmol) and N,N-Dimethylformamide dimethyl acetal (9.21 g, 77.34 mmol) were dissolved in benzene (10 mL). The mixture was heated under reflux for 1 h. The solvent was evaporated and distilled with a Kugelrohr apparatus to give 12 g of ethyl 2-((dimethylamino)methylene)-4,4,4-trifluoro-3-oxobutanoate (yield 65%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 h
  3. customThe solvent was evaporated
  4. distillationdistilled with a Kugelrohr apparatus

Sources & evidence

ORD record
ord-a302a3dda8724160a3a5a9fd05c94c6b
Source dataset
uspto-grants-2013_01
Patent number
US08354436B2

Reaction notes

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