Sodium hydride → 8-Fluoro-4-[2-[4-(i-propyl)phenyl]ethoxy]quinoline

HRID 487129

反応式

HRID 487129 の反応式
[H-].[Na+].Cl[C:4]1[C:13]2[C:8](=[C:9]([F:14])[CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][CH:5]=1.[CH3:15][CH:16]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][OH:26])=[CH:20][CH:19]=1)[CH3:17]>CN(C=O)C.O>[F:14][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[N:7]=[CH:6][CH:5]=[C:4]2[O:26][CH2:25][CH2:24][C:21]1[CH:22]=[CH:23][C:18]([CH:16]([CH3:17])[CH3:15])=[CH:19][CH:20]=1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 82349Benzeneethanol, 4-(1-methylethyl)-HCID 27365874-Chloro-8-fluoroquinoline

生成物 1

HCID 190940598-Fluoro-4-[2-[4-(i-propyl)phenyl]ethoxy]quinoline収率 40.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of 0.96 g of sodium hydride in 10 mL of dry DMF was added 3.6 g of 4-chloro-8-fluoroquinoline. The mixture was cooled in an ice/water bath, and 3.3 g of 2-[4-(1-methylethyl)phenyl]ethyl alcohol was added. The mixture was stirred overnight, then diluted with ice and water. The pH was adjusted to 7, then the product was extracted into CH2Cl2. The CH2Cl2 layer was separated, filtered, and evaporated in vacuo. An azeotrope with xylene was formed to facilitate removal of residual DMF. The residue was chromatographically purified on a silica gel column, eluting with CH2Cl2, →5% EtOAc/CH2Cl2 →10% EtOAc/CH2Cl2. The fractions containing product were combined and evaporated to give an oil, which crystallized on adding ether. Recrystallization yielded 2.5 g of title product. M.P. 56°-60° C.

後処理

  1. temperatureThe mixture was cooled in an ice/water bath
  2. extractionthe product was extracted into CH2Cl2
  3. customThe CH2Cl2 layer was separated
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customAn azeotrope with xylene was formed
  7. customremoval of residual DMF
  8. customThe residue was chromatographically purified on a silica gel column
  9. washeluting with CH2Cl2, →5% EtOAc/CH2Cl2 →10% EtOAc/CH2Cl2
  10. additionThe fractions containing product
  11. customevaporated
  12. customto give an oil, which
  13. customcrystallized
  14. additionon adding ether
  15. customRecrystallization

出典と根拠

ORDレコード
ord-63fbddde773e4bbabf330b2c46962004
出典データセット
uspto-grants-1994_03
特許番号
US05294622

関連ノート

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