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1,6-Dibromohexane → 1-(6-Bromohexyl)-5-methoxy-2-(4-methoxyphenyl)-3-methyl-1H-indole

HRID 981773
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인쇄 미리보기

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HRID 981773 반응식
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)=[C:8]2[CH3:22].[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]Br>CN(C)C=O>[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][N:10]1[C:11]2[C:7](=[CH:6][C:5]([O:4][CH3:3])=[CH:13][CH:12]=2)[C:8]([CH3:22])=[C:9]1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1
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참가 물질

5

반응물 3

HCID 123681,6-DibromohexaneHCID 24758Sodium hydrideHCID 108800612-(4-METHOXYPHENYL)-3-METHYL-5-METHOXYINDOLE

생성물 1

HCID 159256341-(6-Bromohexyl)-5-methoxy-2-(4-methoxyphenyl)-3-methyl-1H-indole수율 84%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

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온도
0 °C

실험 절차

12.5 mmol (300 mg) of NaH are added to 40 ml of absolute dimethylformamide and cooled to 0° C. With vigorous stirring, 7.5 mmol of 5-methoxy-2-(4-methoxy-phenyl)-3-methyl-indole dissolved in 25 ml of absolute dimethylformamide are slowly added dropwise and stirred for 30 minutes at 0° C. This suspension is added dropwise with stirring and ice-cooling to a solution of 11.0 mmol of 1,6-dibromohexane in 25 ml of absolute dimethylformamide and stirred for 30 minutes at 0° C. Excess NaH is destroyed with water and stirring continues for a further 2.5 hours at room temperature. The mixture is shaken with dichloromethane, dried over MgSO4 and the solvent removed. The brown oily crude product is chromatographed on silica gel with dichloro-methane and recrystallized from ethanol. Yield 84%. M.P. 60° C.

후처리

  1. additionare slowly added dropwise
  2. additionThis suspension is added dropwise
  3. stirringwith stirring
  4. stirringstirred for 30 minutes at 0° C
  5. customExcess NaH is destroyed with water
  6. stirringstirring
  7. waitcontinues for a further 2.5 hours at room temperature
  8. stirringThe mixture is shaken with dichloromethane
  9. dry with materialdried over MgSO4
  10. customthe solvent removed
  11. customThe brown oily crude product is chromatographed on silica gel with dichloro-methane
  12. customrecrystallized from ethanol

출처 및 근거

ORD 기록
ord-f307a197ba904e618dca744910ca81de
출처 데이터셋
uspto-grants-1991_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04992553

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