Mono- and dialkylations of pyrrole at C2 and C5 positions by nucleophilic substitution reaction in ionic liquid

Yogesh R Jorapur; Chang-Hee Lee; Dae Yoon Chi

doi:10.1021/ol047446v

Mono- and dialkylations of pyrrole at C2 and C5 positions by nucleophilic substitution reaction in ionic liquid

Org Lett. 2005 Mar 31;7(7):1231-4. doi: 10.1021/ol047446v.

Authors

Yogesh R Jorapur¹, Chang-Hee Lee, Dae Yoon Chi

Affiliation

¹ Department of Chemistry, Inha University, 253 Yonghyundong Namgu, Inchon, 402-751 Korea.

PMID: 15787474
DOI: 10.1021/ol047446v

Abstract

[reaction: see text] A novel ionic liquid methodology for pyrrole C-alkylation is described. The pyrrole alkylation is achieved with various simple alkyl halides and mesylates selectively at C2 and C5 positions in good yields with minimal byproducts under relatively mild conditions in various ionic liquids. 2-(3-Phenylpropyl)pyrrole (2a) was synthesized from pyrrole and 1-bromo-3-phenylpropane in a mixture solvent system, [bmim][SbF6] and CH3CN, in 81% yield at 115 degrees C for 44 h with 5% yield of dialkylated compound 3a.