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

HRID 3385

반응식

HRID 3385 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-39e0ce5ac6fe453c825a8e16562f634e
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733923

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