Journal of Organic Chemistry p. 4409 - 4415 (1984)
Update date:2022-08-04
Topics: Synthesis Column chromatography Yield NMR spectroscopy Recrystallization Nucleophilic substitution Deprotection TLC (thin-layer chromatography) Protecting group Anhydrous conditions Workup Indole Lithiation Electrophilic Aromatic Substitution (EAS) Grignard Reagent Palladium-catalyzed coupling Inert atmosphere Reaction quenching Trimethylsilyl (TMS) group
Barrett, Anthony G. M.
Dauzonne, Daniel
O'Neil, Ian A.
Renaud, Alain
Indole or 1-(trimethylsilyl)indole was reacted sequentially with lithium-chlorotrimethylsilane and with 1,4-benzoquinone to produce 1,4-bis(trimethylsilyl)indole (50 percent and 55 percent, respectively).Methanolysis gave 4-(trimethylsilyl)indole which reacted with electrophiles at C-3.However, the derivative 1-acetyl-4-(trimethylsilyl)indole reacted with acetyl, 2-chloropropanoyl, or propenoyl chlorides via clean C-4 ipso substitution.Attemps to extend the reaction to a useful synthesis of derivatives of 5-oxo-1,3,4,5-tetrahydrobenz
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