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Benzo[b]thiophene derivatives. VII. An abnormal substitution product from 3‐chloromethylbenzo[b]thiophene
Author(s) -
Campaigne E.,
Neiss E. S.
Publication year - 1965
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.5570020303
Subject(s) - thiophene , chemistry , hydroxymethyl , acetonitrile , medicinal chemistry , yield (engineering) , solvent , alkylation , hydrolysis , organic chemistry , catalysis , materials science , metallurgy
The alkylation of cyanide ion with 3‐chloromethylbenzo[b]thiophene gave a higher yield of benzo[b]thiophene‐3‐acetonitrile in dimethyl sulfoxide than in alcohol, and in addition 2‐cyano‐3‐methylbenzo[b]thiophene was obtained as a by‐product in this solvent. The abnormal product was prepared by an alternative, unequivocal synthesis. The isomers were hydrolyzed to their respective acids, which were reduced to 3+(β‐hydroxyethyl)benzo[b]thiophene and 2‐hydroxymethyl‐3‐methylbenzo[b]thiophene. The ultraviolet and nuclear magnetic resonance spectra of these compounds are reported.