Diisopropylamine → 1-(4-Methoxyphenyl)-2-(pyridin-3-yl)ethanone

HRID 1167644

반응식

HRID 1167644 반응식
C(NC(C)C)(C)C.C([Li])CCC.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1.[C:20](OCC)(=[O:29])[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1>O1CCCC1.CCCCCC.O>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([C:20](=[O:29])[CH2:19][C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)=[CH:22][CH:23]=1

참가 물질

8

반응물 4

HCID 7912DiisopropylamineHCID 79703-MethylpyridineHCID 60979Ethyl anisateHCID 178418339Butyllithium

생성물 1

HCID 2383511-(4-Methoxyphenyl)-2-(pyridin-3-yl)ethanone수율 85%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-5 °C

실험 절차

To a stirred solution of diisopropylamine (33.2 mL) in dry tetrahydrofuran (300 mL) cooled at −78° C., was added a solution of 1.6 M n-butyllithium in hexane (148 mL) dropwise. After addition, the resulting mixture was stirred for 10 min at the same temperature, followed by the addition of β-picoline (20 g). The resulting mixture was allowed to warm up to −10-0° C. After an additional 20 min stirring, a solution of ethyl p-anisate (19.4 g) in dry tetrahydrofuran (40 mL) was added. After addition the mixture was stirred for another 1 h at ambient temperature, and water (100 mL) was added to the mixture. The solvent was removed under reduced pressure and the oily product was extracted with ethyl acetate. The extracts were washed with water, dried, and concentrated under reduced pressure. The crystalline residue was recrystallized from ethyl acetate—isopropyl ether to afford the title compound (20.8 g, yield 85%).

후처리

  1. additionAfter addition
  2. stirringAfter an additional 20 min stirring
  3. additionAfter addition the mixture
  4. stirringwas stirred for another 1 h at ambient temperature
  5. customThe solvent was removed under reduced pressure
  6. extractionthe oily product was extracted with ethyl acetate
  7. washThe extracts were washed with water
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. customThe crystalline residue was recrystallized from ethyl acetate—isopropyl ether

출처 및 근거

ORD 기록
ord-7befb63ae11b4039ac8ff22be0107d17
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06620825B1

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