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

HRID 2106015ノート

反応式

HRID 2106015 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
85 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6a9642b30b6244638165638edbbd6acf
出典データセット
uspto-grants-2009_08
特許番号
US07579469B2

反応ノート

読み込み中…