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Synthesis and michael reaction of 3,4‐dimethylpyrrole
Author(s) -
Cheng D. O.,
Bowman T. L.,
Legoff E.
Publication year - 1976
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570130549
Subject(s) - chemistry , methyl vinyl ketone , pyrrole , ketone , catalysis , michael reaction , medicinal chemistry , organic chemistry
A two step synthesis of 3,4‐dimethylpyrrole via the reduction of 3‐carboethoxy‐4‐methyl‐pyrrole is described. Michael addition of methyl vinyl ketone and butyn‐2‐one to 3,4‐dimethylpyrrole gives the bisadducts, 2,5‐bis(3‐oxobutyl)‐3,4‐dimethylpyrrole and 2,5‐bis(3‐oxobutenyl)‐3,4‐dimethylpyrrole, respectively, while ethyl propiolate affords only the monoadduct, ethyl 3‐(3,4‐dimethylpyrrol‐2‐yl)propenoate. Catalytic reduction of the latter ester gives ethyl 3‐(3,4‐dimethylpyrrol‐2‐yl)propanoate which with ethyl propiolate gives ethyl 3‐(5‐carbethoxyethyl‐3,4‐dimethyl‐2‐yl)propenoate.