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

HRID 3338

Reaktionsgleichung

Reaktionsgleichung von HRID 3338
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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b929091e25a74504966cd0bf54a67e49
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733923

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