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

HRID 1533432

反応式

HRID 1533432 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-df3fd70865594936b4b5343da0b59d16
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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