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

HRID 1533430

반응식

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

참가 물질

4

반응물 2

HCID 67793Ethyl 4,4,4-trifluoroacetoacetate2회HCID 53979199Butanoic acid, 2-[(dimethylamino)methylene]-4,4,4-trifluoro-3-oxo-, ethyl ester3회

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-89da67ca858c46daa210cb3d4801029b
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06207828B1

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