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Pyridine → Ethyl 2-isonicotinoyl-3-oxobutanoate

HRID 1011958
ノート
印刷プレビュー

反応式

HRID 1011958 の反応式
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[Cl-].[Mg+2].[Cl-].N1C=CC=CC=1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1>C(Cl)Cl>[CH2:8]([O:7][C:1](=[O:6])[CH:2]([C:19]([C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1)=[O:26])[C:3](=[O:4])[CH3:5])[CH3:9]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 1049PyridineHCID 8868Ethyl AcetoacetateHCID 417436Pyridine-4-carbonyl chlorideHCID 5360315Magnesium Chloride

生成物 1

HCID 67314215Ethyl 2-isonicotinoyl-3-oxobutanoate収率 47%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

8 g (61.5 mmol) of ethyl acetoacetate were dissolved in 280 ml of CH2Cl2, the solution was cooled at 0° C. and successively were added 6.00 g (63.3 mmol) of anhydrous magnesium chloride, 10 ml (124 mmol) of pyridine and 13.4 g (94.73 mmol) of isonicotinoyl chloride. The yellow suspension was stirred 1 h under ice cooling and 18 h at room temperature. The reaction mixture was poured into crashed ice and extracted twice with CH2Cl2. The organic phases were washed with brine, dried over magnesium sulfate, and evaporated. The residue was purified by column chromatography (n-heptane:EtOAc 1:4) to afford the title compound as light yellow oil (6.75 g, 47%). MS: 236.0 (MH+).

後処理

  1. additionThe reaction mixture was poured
  2. extractionextracted twice with CH2Cl2
  3. washThe organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by column chromatography (n-heptane:EtOAc 1:4)

出典と根拠

ORDレコード
ord-afc972fc7b7a4294870cd409cba3560f
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07977358B2

反応ノート

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