Triethylamine → Ethyl 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 422753ノート

反応式

HRID 422753 の反応式
C(N(CC)CC)C.[CH2:8]([O:10][C:11]([C:13]1[C:18](O)=[CH:17][C:16](=[O:20])[N:15]([CH3:21])[CH:14]=1)=[O:12])[CH3:9].O=P(Cl)(Cl)[Cl:24]>>[CH2:8]([O:10][C:11]([C:13]1[C:18]([Cl:24])=[CH:17][C:16](=[O:20])[N:15]([CH3:21])[CH:14]=1)=[O:12])[CH3:9]

参加物

4

反応物 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 54685351Ethyl 4-hydroxy-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

生成物 1

HCID 11615451Ethyl 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate収率 67%

実験手順

Triethylamine (7.07 mL, 50.7 mmol) was added to a suspension of 4-hydroxy-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester (10.0 g, 50.7 mmol) and POCl3 (27.85 mL, 304.3 mmol). After stirring 16 hours, the reaction mixture was concentrated under reduced pressure. The resulting residue was poured onto ice, carefully neutralized with saturated K2CO3 solution, and diluted with EtOAc. The layers were separated and the aqueous phase further extracted with EtOAc. The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure to yield 7.3 g (67%) clean desired product.

後処理

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionThe resulting residue was poured onto ice
  3. additiondiluted with EtOAc
  4. customThe layers were separated
  5. extractionthe aqueous phase further extracted with EtOAc
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-da377c1ef3254a5da209872999502156
出典データセット
uspto-grants-2012_01
特許番号
US08101639B2

反応ノート

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