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

HRID 359323

반응식

HRID 359323 반응식
[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

참가 물질

5

반응물 3

HCID 7762Ethyl butyrateHCID 69188Ethyl NicotinateHCID 2723922Sodium ethoxide

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6ede371724bf47e7a016b39475c4275e
출처 데이터셋
uspto-grants-1991_03
특허 번호
US05000946

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