Reaktion #3463

ord-1b52bb60c1944a8bb041ea0a07e47ab6

Reaktionsgleichung

CCc1cc2c(OC)cccc2n1Cc1ccccc1-c1ccccc1
1-([1,1'-biphenyl]-2-ylmethyl)-2-ethyl-4-methoxy-1H-indole
ClCl
Cl2
CCc1cc2c(O)cccc2n1Cc1ccccc1-c1ccccc1
1-([1,1'-biphenyl]-2-ylmethyl)-2-ethyl-4-hydroxy-1H-indole
Ausbeute 69.3%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe crude product was chromatographed on silica gel
  2. 2
    Wascheneluted with 20% EtOAc/hexane

Vorschrift

By the method used in Example 1, Part D, 911 mg (2.6 mmol) of 1-([1,1'-biphenyl]-2-ylmethyl)-2-ethyl-4-methoxy-1H-indole was O-demethylated by treating it with 10 mL of 1M BBr3 /CH2 Cl2. The crude product was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 590 mg (69% yield) of 1-([1,1'-biphenyl]-2-ylmethyl)-2-ethyl-4-hydroxy-1H-indole as an oil.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05733923uspto-grants-1998_03