Sodium ethoxide → 1-[4-(5-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one

HRID 2106015노트

반응식

HRID 2106015 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([C:8]([CH3:18])([CH3:17])[CH2:9][C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][O:11]2)[CH:7]=1.[OH:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=[CH:24][CH:23]=1.[O-]CC.[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([C:8]([CH3:18])([CH3:17])[CH2:9][C:10]([OH:11])([C:13]([F:16])([F:15])[F:14])[CH2:12][N:25]2[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:22](=[O:21])[CH:23]=[CH:24]2)[CH:7]=1

참가 물질

5

반응물 3

HCID 2723922Sodium ethoxideHCID 578097532-[2-(5-Bromo-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxiraneHCID 178516385quinolin-4-ol

생성물 1

HCID 578097571-[4-(5-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one수율 73.5%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
85 °C

실험 절차

A mixture of 2-[2-(5-bromo-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (5.0 g, 14.2 mmol), 4-hydroxyquinoline (3.08 g, 21.2 mmol) and sodium ethoxide (21 wt. % solution in ethanol, 5.3 mL, 14.2 mmol) in ethanol (120 mL) was heated at 85° C. for 14 hours. The reaction was quenched with water and concentrated in vacuo to remove most of the ethanol. The residue was diluted with methylene chloride and washed with half saturated sodium bicarbonate (NaHCO3), dried over magnesium sulfate, filtered, and concentrated in vacuo. The product was precipitated from diethyl ether-hexanes to afford 1-[4-(5-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one (5.2 g, 73% yield).

후처리

  1. customThe reaction was quenched with water
  2. concentrationconcentrated in vacuo
  3. customto remove most of the ethanol
  4. additionThe residue was diluted with methylene chloride
  5. washwashed with half saturated sodium bicarbonate (NaHCO3)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe product was precipitated from diethyl ether-hexanes

출처 및 근거

ORD 기록
ord-6a9642b30b6244638165638edbbd6acf
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07579469B2

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