Epoxymethylation of Pyrroles with Epichlorohydrin

SCHEME 2.127 Synthesis of N-ethynylpyrrole via the reaction of pyrrole with 1,2-dichloroethene in the KOH/DMSO system. 

SCHEME 2.128 Synthesis of N-ethynylpyrrole from pyrrole and trichloroethene. 

SCHEME 2.129 Synthesis of N-glycidyl-4,5,6,7-tetrahydroindole by epoxymethylation of 4,5,6,7-terahydroindole with epichlorohydrin. 

Alkylation of 4,5,6,7-tetrahydroindole with epichlorohydrin in the presence of alkaline metal hydroxides MOH (M=Na, K) proceeds with low efficiency (the yield of the prodncts does not exceed 25%). 

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A method for epoxymethylation of pyrroles with epichlorohydrin has been elaborated. N-Glycidyl-4,5,6,7-tetrahydroindole (Table 2.14), a perspective modifying agent of epoxy resins, is synthesized by the reaction of sodium or potassium derivatives (obtained from 4,5,6,7-tetrahydroindole and NaOH or KOH with azeotropic removal of water) and epichlorohydrin (toluene, benzene, xylene) (Scheme 2.129) [599]. 

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