Ethyl butyrate → 1-(Pyridin-3-yl)butan-1-one

HRID 359323

反応式

HRID 359323 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](OCC)(=O)[CH2:13][CH2:14]C.[O-]CC.[Na+]>O>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:1]([CH2:12][CH2:13][CH3:14])=[O:9])[CH:3]=1

参加物

5

反応物 3

HCID 7762Ethyl butyrateHCID 69188Ethyl NicotinateHCID 2723922Sodium ethoxide

生成物 1

HCID 4595021-(Pyridin-3-yl)butan-1-one

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of ethyl nicotinate (15.1 g, 0.1 mole), ethyl butyrate (17.4 g, 0.15 mole) and sodium ethoxide (10.2 g, 0.15 mole) was stirred and heated under nitrogen at 100°C. for five hours. After cooling, the mixture was diluted with water (150 ml), extracted with diethyl ether (50 ml) and the aqueous layer made acidic to pH1 with concentrated hydrochloric acid (50 ml). The aqueous layer was heated at 90°C. for 2 hours, cooled, and made alkaline with solid potassium carbonate and extracted with diethyl ether (3×75 ml). The dried (magnesium sulphate) organic layer was concentrated and distilled to give propyl 3-pyridyl ketone (b.pt. 118-120°C./14 mm Hg).

後処理

  1. temperatureAfter cooling
  2. extractionextracted with diethyl ether (50 ml)
  3. temperatureThe aqueous layer was heated at 90°C. for 2 hours
  4. temperaturecooled
  5. extractionextracted with diethyl ether (3×75 ml)
  6. dry with materialThe dried (magnesium sulphate) organic layer
  7. concentrationwas concentrated
  8. distillationdistilled

出典と根拠

ORDレコード
ord-6ede371724bf47e7a016b39475c4275e
出典データセット
uspto-grants-1991_03
特許番号
US05000946

関連ノート

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