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

HRID 1533433

Reaktionsgleichung

Reaktionsgleichung von HRID 1533433
[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.[CH3:16][N:17]([CH:19](OC)OC)[CH3:18].O>C1COCC1>[F:1][C:2]([F:11])([F:12])[C:3]([C:4](=[CH:16][N:17]([CH3:19])[CH3:18])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:10]

Komponenten

6

Edukt 4

HCID 284Formic AcidHCID 962WaterHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 78373Dimethylformamide dimethyl acetal

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred mixture of ethyl trifluoroacetoacetate (4.6 g, 0.025 mol) and formic acid (2.3 g, 0.05 mol) in 15 ml of THF, DMF dimethyl acetal (6.2 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 45 minutes 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 major product; 3.2 g (53%). Ethyl 3-(N,N-dimethylamino)-2-propenoate (Compound 4, Rf=0.5) was obtained as the minor product in the form of an oil; 0.85 g (23.7%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-73f996b722e44a5081fad080e64cd604
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06207828B1

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