4-methoxy-2-methyl-1-(phenylmethyl)-1H-indole → 1-Benzyl-2-methyl-1H-indol-4-ol

HRID 3338

반응식

HRID 3338 반응식
C[O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([CH3:19])[N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[OH:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([CH3:19])[N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

4

반응물 2

HCID 107771474-methoxy-2-methyl-1-(phenylmethyl)-1H-indoleHCID 22277759Boron tribromide dichloromethane

생성물 1

HCID 107523601-Benzyl-2-methyl-1H-indol-4-ol수율 49%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 1.25 g (5 mmol) of 4-methoxy-2-methyl-1-(phenylmethyl)-1H-indole and 20 mL of 1M BBr3 /CH2Cl2 in 50 mL of methylene chloride was stirred at room temperature for 5 hours and concentrated at reduced pressure. The residue was dissolved in ethyl acetate, washed with brine and dried (MgSO4). After concentrating at reduced pressure, the residue was chromatographed on silica gel eluting with 20% EtOAc/hexane to give 577 mg (49% yield) of 4-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole, 125°-127° C.

후처리

  1. concentrationconcentrated at reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationAfter concentrating at reduced pressure
  6. customthe residue was chromatographed on silica gel eluting with 20% EtOAc/hexane

출처 및 근거

ORD 기록
ord-b929091e25a74504966cd0bf54a67e49
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733923

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