Ethyl 4,4,4-trifluoroacetoacetate → Ethyl 3-(N,N-dimethylamino)acrylate

HRID 1533430ノート

反応式

HRID 1533430 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>C(O)(=O)C>[CH3:13][N:12]([CH:11]=[CH:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:14]

参加物

4

反応物 2

HCID 67793Ethyl 4,4,4-trifluoroacetoacetate2 回HCID 53979199Butanoic acid, 2-[(dimethylamino)methylene]-4,4,4-trifluoro-3-oxo-, ethyl ester3 回

生成物 1

HCID 121015Ethyl 3-(N,N-dimethylamino)acrylate

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

I have found surprisingly conditions which allow the preparation of ethyl 2-trifluoroacetyl-3-(N,N-dimethylamino)-2-propenoate (2) from ethyl trifluoroacetoacetate and DMF acetals according to a general one-step reaction. Specifically, I found that compound 2 can be prepared in good yields (61-85%) by reacting ethyl trifluoroacetoacetate with DMF acetals in the presence of an organic acid such as acetic acid. While not wishing to be bound by theory, the success of this reaction condition appears to lie in the suppression of the loss of the trifluoroacetyl group from (2) through the attack of the alcohol by-products. In the absence of the organic acid, ethyl 3-(N,N-dimethylamino)-2-propenoate (4) is formed as the major product in all cases. My overall result is shown in Scheme 2.

後処理

  1. customto a general one-step reaction
  2. customcan be prepared
  3. customin good yields (61-85%)

出典と根拠

ORDレコード
ord-89da67ca858c46daa210cb3d4801029b
出典データセット
uspto-grants-2001_03
特許番号
US06207828B1

反応ノート

読み込み中…