Benzyl Bromide → 4-(phenylmethoxy)-1H-indole

HRID 430773

반응식

HRID 430773 반응식
[OH-].[K+].[OH:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[CH2:13]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

5

반응물 3

HCID 7498Benzyl Bromide2회HCID 14797Potassium HydroxideHCID 754211H-indol-4-ol

생성물 1

HCID 884654-(phenylmethoxy)-1H-indole수율 85%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Potassium hydroxide (0.42 g) was added to 4-hydroxyindole (1.00 g) in DMF (25 ml), and the solution was stirred at room temperature for 15 minutes. Benzyl bromide (1.00 ml) was added to the solution, and the solution was stirred at room temperature for 1.5 hours. Since the reaction was not completed, benzyl bromide (0.20 ml) was further added and the solution was stirred for 5 hours. After removing the solvent under reduced pressure, water (50 ml) was added to the residue and the resultant was extracted with ether (3×50 ml). The organic layers were washed with saturated brine, and dried over sodium sulfate. After removing solids by filtration, the solvent was removed under reduced pressure and the obtained crude product was purified by silica gel column chromatography to obtain the desired product (1.43 g, yield: 85%).

후처리

  1. stirringthe solution was stirred at room temperature for 1.5 hours
  2. stirringthe solution was stirred for 5 hours
  3. customAfter removing the solvent under reduced pressure, water (50 ml)
  4. additionwas added to the residue
  5. extractionthe resultant was extracted with ether (3×50 ml)
  6. washThe organic layers were washed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. customAfter removing solids
  9. filtrationby filtration
  10. customthe solvent was removed under reduced pressure
  11. customthe obtained crude product
  12. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-ded0112ca83f4afa952d72e5c70ce665
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323235B1

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