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

HRID 2304595

反応式

HRID 2304595 の反応式
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

参加物

8

反応物 4

HCID 7912DiisopropylamineHCID 79703-MethylpyridineHCID 60979Ethyl anisateHCID 178418339Butyllithium

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-5 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-8f42e5e64998400cb5d73dd2a29a7034
出典データセット
uspto-grants-2002_08
特許番号
US06436966B1

関連ノート

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