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

HRID 487129

반응식

HRID 487129 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-63fbddde773e4bbabf330b2c46962004
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05294622

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