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

HRID 1533431

反応式

HRID 1533431 の反応式
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]

参加物

5

反応物 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

生成物 1

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

実験手順

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.

後処理

  1. customMy result

出典と根拠

ORDレコード
ord-d9087534728c4894a67931609e177ef0
出典データセット
uspto-grants-2001_03
特許番号
US06207828B1

関連ノート

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