Acetic Acid → Butanoic acid, 2-[(dimethylamino)methylene]-4,4,4-trifluoro-3-oxo-, ethyl ester

HRID 1533432

반응식

HRID 1533432 반응식
[F:1][C:2]([F:12])([F:11])[C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].C(O)(=O)C.[CH3:17][N:18]([CH:20]=O)[CH3:19]>O>[F:1][C:2]([F:11])([F:12])[C:3]([C:4](=[CH:17][N:18]([CH3:20])[CH3:19])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:10]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 67793Ethyl 4,4,4-trifluoroacetoacetate

생성물 1

HCID 53979199Butanoic acid, 2-[(dimethylamino)methylene]-4,4,4-trifluoro-3-oxo-, ethyl ester

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a stirred mixture of ethyl trifluoroacetoacetate (4.6 g, 0.025 mol) and acetic acid (3.0 g, 0.05 mol) at room temperature, DMF diusopropyl acetal (8.75 g, 0.05 mol) was added dropwise at a rate which maintained the reaction temperature below 35° C. After stirring the mixture at ambient temperature for 2 hours to complete the reaction (TLC), it was poured into water and extracted with ether. The ether extract was washed with water, brine solution, then dried (MgSO4), and concentrated. The residual yellow oil was column-chromatographed on silica gel (Hexanes:Ethyl acetate/7:3) to give ethyl 2-trifluoroacetyl-3-(N,N-dimethylamino)-2-propenoate (Compound 2; Rf=0.3) as the main product; 4.5 g (75%).

후처리

  1. temperaturemaintained the reaction temperature below 35° C
  2. customthe reaction (TLC), it
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washwas washed with water, brine solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residual yellow oil was column-chromatographed on silica gel (Hexanes:Ethyl acetate/7:3)

출처 및 근거

ORD 기록
ord-df3fd70865594936b4b5343da0b59d16
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06207828B1

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