Benzyl Bromide → 1H-Indol-5-ol, 1-(phenylmethyl)-

HRID 3385

反応式

HRID 3385 の反応式
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:7]=[CH:6]2

参加物

6

反応物 4

HCID 7498Benzyl BromideHCID 138725-MethoxyindoleHCID 24758Sodium hydrideHCID 22277759Boron tribromide dichloromethane

生成物 1

HCID 107754621H-Indol-5-ol, 1-(phenylmethyl)-収率 19%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-5 °C

実験手順

5-Methoxy-1H-indole (5.6 g, 21.5 mmol) was reacted with 1.0 g (25 mmol) of 60% sodium hydride and then 3.0 mL (25 mmol) of benzyl bromide by the method described in Example 12, Part D to give crude 5-methoxy-1-(phenylmethyl)-1H-indole. This material was dissolved in 250 mL of methylene chloride, cooled to -5° C., 50 mL of 1M BBr3 /CH2Cl2 added, the cooling bath removed and the mixture stirred for 1.75 hours. Ice water was added and the mixture stirred. The organic layer was separated, washed with saturated NaCl, dried (Na2 SO4), and concentrated at reduced pressure. The residue was chromatographed on silica gel and eluted with 20% ether/hexane→ether to give 870 mg (19% overall yield) of crude 5-hydroxy-1-(phenylmethyl)-1H-indole.

後処理

  1. customto give crude 5-methoxy-1-(phenylmethyl)-1H-indole
  2. customthe cooling bath removed
  3. additionIce water was added
  4. stirringthe mixture stirred
  5. customThe organic layer was separated
  6. washwashed with saturated NaCl
  7. customdried (Na2 SO4)
  8. concentrationconcentrated at reduced pressure
  9. customThe residue was chromatographed on silica gel
  10. washeluted with 20% ether/hexane

出典と根拠

ORDレコード
ord-39e0ce5ac6fe453c825a8e16562f634e
出典データセット
uspto-grants-1998_03
特許番号
US05733923

関連ノート

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