反応 #3455

ord-ac45098226724296a2030ef33a83f824

反応方程式

COc1cccc2c1cc(C)n2Cc1cccc2ccccc12
4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole
BrB(Br)Br.ClCCl
BBr3 CH2Cl2
Cc1cc2c(O)cccc2n1Cc1cccc2ccccc12
4-hydroxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole
収率 71.0%

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他to give a material that
  2. 2
    その他was chromatographed on silica gel (
  3. 3
    洗浄eluted with 20% EtOAc/hexane

実験手順

By the method used in Example 1, Part D, 1.17 g (3.9 mmol) of 4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole was O-demethylated by treating it with 15.6 mL of 1M BBr3 /CH2Cl2 to give a material that was chromatographed on silica gel (eluted with 20% EtOAc/hexane then 50% EtOAc/hexane) to give 796 mg (71% yield) of 4-hydroxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US05733923uspto-grants-1998_03