Ethyl isonicotinate → 2-Cyano-2-[4-(1,1-dimethylethyl)phenyl]-1-(4-pyridyl)ethanone

HRID 2304604

반응식

HRID 2304604 반응식
[C:1]([O:9]CC)(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH3:12][C:13]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]#[N:24])=[CH:18][CH:17]=1)([CH3:15])[CH3:14].CC(C)([O-])C.[K+]>C(O)(C)(C)C.O>[C:23]([CH:22]([C:19]1[CH:20]=[CH:21][C:16]([C:13]([CH3:15])([CH3:14])[CH3:12])=[CH:17][CH:18]=1)[C:1]([C:2]1[CH:3]=[CH:4][N:5]=[CH:6][CH:7]=1)=[O:9])#[N:24]

참가 물질

6

반응물 3

HCID 15291Ethyl isonicotinateHCID 76784(4-tert-Butylphenyl)acetonitrileHCID 23665647Potassium tert-butoxide

생성물 1

HCID 229937442-Cyano-2-[4-(1,1-dimethylethyl)phenyl]-1-(4-pyridyl)ethanone수율 35%

시약·촉매·용매 2

HCID 962Water용매HCID 6386tert-Butanol용매

반응 조건

온도
100 °C

실험 절차

To a solution of ethyl isonicotinate (12 g) and 4-(1,1-Dimethylethyl)phenylacetonitrile (9.1 g) in tert-butyl alcohol (36 mL), was added potassium tert-butoxide (7.3 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 extract was washed with water, dried, And the solvent was evaporated. The crystalline residue was recrystallized from ethyl acetate-isopropyl ether to obtain 2-cyano-2-[4-(1,1-dimethylethyl)phenyl]-1-(4-pyridyl)ethanone (5.09 g, yield 35%).

후처리

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

출처 및 근거

ORD 기록
ord-603c61fb75154f07ba90e9b15f3dfddd
출처 데이터셋
uspto-grants-2002_08
특허 번호
US06436966B1

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