Preparation and Reactions of 4-(Trimethylsilyl)indole

Article abstract of DOI:10.1021/jo00197a016

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-tetrahydrobenzindole, a lysergic acid synthon, were prevented by low yields.