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

HRID 1533431노트

반응식

HRID 1533431 반응식
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]

참가 물질

5

반응물 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

생성물 1

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

실험 절차

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.

후처리

  1. customMy result

출처 및 근거

ORD 기록
ord-d9087534728c4894a67931609e177ef0
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06207828B1

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