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

HRID 1533431Notes

Reaction equation

HRID 1533431 reaction equation
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]

Participants

5

Reactant 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

Product 1

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

Procedure

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.

Workup

  1. customMy result

Sources & evidence

ORD record
ord-d9087534728c4894a67931609e177ef0
Source dataset
uspto-grants-2001_03
Patent number
US06207828B1

Reaction notes

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