p-Toluenesulfonic acid → Ethyl 3-(N,N-dimethylamino)acrylate

HRID 1533431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1533431
FC(F)(F)C([C:5](=[CH:11][N:12]([CH3:14])[CH3:13])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=O.FC(F)(F)C(=O)CC(OCC)=O.CN(C(OC)OC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:13][N:12]([CH:11]=[CH:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:14]

Komponenten

5

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 78373Dimethylformamide dimethyl acetalHCID 53979199Butanoic acid, 2-[(dimethylamino)methylene]-4,4,4-trifluoro-3-oxo-, ethyl ester

Produkt 1

HCID 121015Ethyl 3-(N,N-dimethylamino)acrylateAusbeute 75 %

Versuchsvorschrift

My result is especially surprising in view of the results reported by Beck et al., vide supra, who attempted to prepare (2) by reacting ethyl trifluoroacetoacetate with DMF dimethyl acetal in the presence of a catalytic quantity of p-toluenesulfonic acid. The reaction resulted in the formation of ethyl 3-(N,N-dimethylamino)-2-propenoate (4) in 75% yield. Presumably, the methanol by-product further reacted with the target compound (2) to give the unexpected product and methyl trifluoroacetate.

Aufarbeitung

  1. customMy result

Quellen und Nachweise

ORD-Eintrag
ord-d9087534728c4894a67931609e177ef0
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06207828B1

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