Acetone → 1-(2-Cyanoisonicotinyl)-1,3-butanedione

HRID 1635501

反応式

HRID 1635501 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][N:12]=1)[C:6](OC)=O)#[N:2].[CH3:13][C:14]([CH3:16])=[O:15].[CH3:17][O-:18].[Na+]>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][N:12]=1)[CH2:6][C:17](=[O:18])[CH2:13][C:14](=[O:15])[CH3:16])#[N:2]

参加物

5

反応物 3

HCID 180AcetoneHCID 10942334Sodium MethoxideHCID 12132796Methyl 2-cyanopyridine-4-carboxylate

生成物 1

HCID 544384121-(2-Cyanoisonicotinyl)-1,3-butanedione収率 58%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
35 °C

実験手順

To a solution of methyl 2-cyanoisonicotinate (20.0 g, 0.126 mol) in 250 mL THF was added acetone (30.6 mL, 0.42 mol). The solution was warmed to 35° C. and sodium methoxide (7.15 g, 0.132 mol) was added portionwise over 20 minutes. The mixture was heated at reflux for 16 hours. The solvent was removed in vacuo and the residue was dissolved in water, acidified to pH=6 with acetic acid. The aqueous phase was extracted with ethyl acetate and the organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to yield 13.0 g (58% yield) of product as a brown solid, which was used in next step without purification.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 hours
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in water
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. washthe organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-605ada101eb74710a60f749723efbd6f
出典データセット
uspto-grants-2003_01
特許番号
US06509361B1

関連ノート

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