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

HRID 1533432

Reaktionsgleichung

Reaktionsgleichung von HRID 1533432
[F:1][C:2]([F:12])([F:11])[C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].C(O)(=O)C.[CH3:17][N:18]([CH:20]=O)[CH3:19]>O>[F:1][C:2]([F:11])([F:12])[C:3]([C:4](=[CH:17][N:18]([CH3:20])[CH3:19])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:10]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 67793Ethyl 4,4,4-trifluoroacetoacetate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred mixture of ethyl trifluoroacetoacetate (4.6 g, 0.025 mol) and acetic acid (3.0 g, 0.05 mol) at room temperature, DMF diusopropyl acetal (8.75 g, 0.05 mol) was added dropwise at a rate which maintained the reaction temperature below 35° C. After stirring the mixture at ambient temperature for 2 hours to complete the reaction (TLC), it was poured into water and extracted with ether. The ether extract was washed with water, brine solution, then dried (MgSO4), and concentrated. The residual yellow oil was column-chromatographed on silica gel (Hexanes:Ethyl acetate/7:3) to give ethyl 2-trifluoroacetyl-3-(N,N-dimethylamino)-2-propenoate (Compound 2; Rf=0.3) as the main product; 4.5 g (75%).

Aufarbeitung

  1. temperaturemaintained the reaction temperature below 35° C
  2. customthe reaction (TLC), it
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washwas washed with water, brine solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residual yellow oil was column-chromatographed on silica gel (Hexanes:Ethyl acetate/7:3)

Quellen und Nachweise

ORD-Eintrag
ord-df3fd70865594936b4b5343da0b59d16
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06207828B1

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