Phenylacetonitrile → beta-Oxo-alpha-phenyl-3-pyridinepropanenitrile

HRID 1167645ノート

反応式

HRID 1167645 の反応式
[C:1]([O:9]CC)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[C:12]1([CH2:18][C:19]#[N:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC(C)([O-])C.[K+]>C(O)(C)(C)C.O>[C:19]([CH:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:9])#[N:20]

参加物

6

反応物 3

HCID 8794PhenylacetonitrileHCID 69188Ethyl NicotinateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 3765543beta-Oxo-alpha-phenyl-3-pyridinepropanenitrile収率 62%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6386tert-Butanol溶媒

反応条件

温度
100 °C

実験手順

To a solution of ethyl nicotinate (10 g) and phenylacetonitrile (5.1 g) in tert-butyl alcohol (30 mL), was added potassium tert-butoxide (6.4 g), and the mixture was stirred at 100° C. for 3 h. After cooling, the resulting mixture was dissolved in water and washed with isopropyl ether. The aqueous phase was adjusted to pH 7.0 with 2 N hydrochloric acid and extracted with ethyl acetate. The extracts were washed with water, dried, and the solvent was evaporated. The crystalline residue was recrystallized from ethyl acetate-isopropyl ether to obtain the title compound (6.0 g, yield 62%).

後処理

  1. temperatureAfter cooling
  2. washwashed with isopropyl ether
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with water
  5. customdried
  6. customthe solvent was evaporated
  7. customThe crystalline residue was recrystallized from ethyl acetate-isopropyl ether

出典と根拠

ORDレコード
ord-ce1f39d40dc6494e99758909089d0bc2
出典データセット
uspto-grants-2003_09
特許番号
US06620825B1

反応ノート

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