Preparation of 2 substituted pyrroles and indoles by regioselective alkylation and deprotection of 1 2 trimethylsilylethoxymethyl pyrrole and 1 2 trimethylsilyethoxymethyl indole
Edwards, M.P.; Doherty, A.M.; Ley, S.V.; Organ, H.M.
Tetrahedron 42(13): 3723-3729
ISSN/ISBN: 0040-4020 Accession: 006172416
After N-alkylation of pyrrole and indole with 2-trimethylsilylethoxymethyl chloride the products of the reaction could be regioselectively deprotonated with n-butyllithium at the 2-position. Reaction of the resulting anions with acid chlorides, lactones, silyl chlorides or aldehydes gave addition products, some of which were deprotected to the parent pyrrole or indole using anhydrous tetra-n-butylammonium fluoride.