Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (E)-Ethyl 3-(6-chloro-4-(methylamino)pyridin-3-yl)acrylate

HRID 710579ノート

反応式

HRID 710579 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=O)=[C:4]([NH:10][CH3:11])[CH:3]=1.[C:12]([CH:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:14][CH2:15][CH3:16])=[O:13]>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:17]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:4]([NH:10][CH3:11])[CH:3]=1

参加物

4

反応物 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 234345716-Chloro-4-(methylamino)nicotinaldehyde

生成物 1

HCID 86686188(E)-Ethyl 3-(6-chloro-4-(methylamino)pyridin-3-yl)acrylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 6-chloro-4-(methylamino)pyridine-3-carboxaldehyde (3.41 g, 20 mmol) in THF (120 mL) was added (carbethoxymethylene)triphenylphosphorane (8.35 g, 24 mmol). The mixture was heated at reflux for 16 h, and was then cooled and concentrated. The residue was chromatographed on silica gel (12% ethyl acetate in hexanes eluant) to provide the title compound. MS (m/z) 241.0 (M+1).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 h
  3. temperaturewas then cooled
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel (12% ethyl acetate in hexanes eluant)

出典と根拠

ORDレコード
ord-a484fae59d4b4f3397004f0e33a035de
出典データセット
uspto-grants-2015_11
特許番号
US09181238B2

反応ノート

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