4-Iodophenol → 2-((4-Iodophenoxy)methyl)-6-phenoxypyridine

HRID 384102노트

반응식

HRID 384102 반응식
[O:1]([C:8]1[N:13]=[C:12]([CH2:14][OH:15])[CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:16][C:17]1[CH:22]=[CH:21][C:20](O)=[CH:19][CH:18]=1.[H-].[Na+]>C(OCC)(=O)C.C(N(CC)CC)C.CS(Cl)(=O)=O.CN(C)C=O>[I:16][C:17]1[CH:22]=[CH:21][C:20]([O:15][CH2:14][C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[N:13]=2)=[CH:19][CH:18]=1

참가 물질

8

반응물 3

HCID 108944-IodophenolHCID 24758Sodium hydrideHCID 128791556-Phenoxy-2-pyridinemethanol

생성물 1

HCID 684313182-((4-Iodophenoxy)methyl)-6-phenoxypyridine

시약·촉매·용매 4

HCID 6228Dimethylformamide용매2회HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매2회HCID 31297Methanesulfonyl chloride용매

반응 조건

온도
0 °C

실험 절차

To a solution of (6-phenoxypyridin-2-yl)methanol (100 mg) in ethyl acetate (4 ml), triethylamine (0.103 ml) and methanesulfonyl chloride (0.062 ml) were added under ice-cooling, the reaction solution was stirred at the same temperature for 1 hour. The reaction solution was diluted with ethyl acetate, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to afford a crude product as a brown oil. To a solution of 4-iodophenol in dimethylformamide (1 ml), 24 mg of sodium hydride was added under ice-cooling, and the reaction solution was stirred at room temperature for 1 hour. The reaction solution was cooled to 0° C., a solution of the crude product in dimethylformamide (1 ml) was added, and the reaction solution was stirred at room temperature for 2 hours. The reaction solution was diluted with a saturated saline solution, extracted with diethyl ether, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-20:80)) to afford the title compound as a white solid.

후처리

  1. temperaturecooling
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customto afford a crude product as a brown oil
  6. temperaturecooling
  7. stirringthe reaction solution was stirred at room temperature for 1 hour
  8. stirringthe reaction solution was stirred at room temperature for 2 hours
  9. additionThe reaction solution was diluted with a saturated saline solution
  10. extractionextracted with diethyl ether
  11. dry with materialdried over anhydrous magnesium sulfate
  12. distillationThe solvent was distilled off under reduced pressure
  13. customthe residue obtained
  14. customwas purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-20:80))

출처 및 근거

ORD 기록
ord-46244cd2cfdf477b8dc7f8be46f59ce5
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367708B2

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