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

HRID 430773ノート

反応式

HRID 430773 の反応式
[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

参加物

5

反応物 3

HCID 7498Benzyl Bromide2 回HCID 14797Potassium HydroxideHCID 754211H-indol-4-ol

生成物 1

HCID 884654-(phenylmethoxy)-1H-indole収率 85%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-ded0112ca83f4afa952d72e5c70ce665
出典データセット
uspto-grants-2001_11
特許番号
US06323235B1

反応ノート

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