2-Butenoic acid, 3-amino-, ethyl ester, (2Z)- → Ethyl 2-methyl-4-(trifluoromethyl)-6-(4-(trifluoromethyl)phenyl)nicotinate

HRID 890473ノート

反応式

HRID 890473 の反応式
[F:1][C:2]([F:19])([F:18])/[C:3](/O)=[CH:4]/[C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)=O.[CH2:20]([O:22][C:23](=[O:28])/[CH:24]=[C:25](\[NH2:27])/[CH3:26])[CH3:21]>C(#N)C>[CH2:20]([O:22][C:23](=[O:28])[C:24]1[C:3]([C:2]([F:19])([F:18])[F:1])=[CH:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)=[N:27][C:25]=1[CH3:26])[CH3:21]

参加物

4

反応物 2

HCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 178520887HCID 178520887、化合物

生成物 1

HCID 86597779Ethyl 2-methyl-4-(trifluoromethyl)-6-(4-(trifluoromethyl)phenyl)nicotinate収率 35%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To an acetonitrile (50 ml) solution of (Z)-4,4,4-trifluoro-3-hydroxy-1-(4-trifluoromethyl-phenyl)-but-2-en-1-one (4.7 g, 17 mmol; D. Barrett, P. D. Bentley, T. R. Perrior, Synthetic Commun. 1996, 26, 3401–3406) was added ethyl-3-aminocrotonate (4.27 g, 33 mmol) under an argon atmosphere. The mixture was heated at reflux for 12 h. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, n-heptane/ethyl acetate) to yield 2.2 g (5.8 mmol, 35%) of the title compound as yellow crystals.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 12 h
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by column chromatography (silica gel, n-heptane/ethyl acetate)

出典と根拠

ORDレコード
ord-7b2a2b51e622453b9cc629fa565e5ec8
出典データセット
uspto-grants-2006_02
特許番号
US06995263B2

反応ノート

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