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Synthesis of 4‐alkyl‐3‐pyridinols from 3‐benzyloxypyridine
Author(s) -
Comins Daniel L.,
Stroud Eric D.
Publication year - 1985
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.5570220559
Subject(s) - chemistry , alkyl , chloranil , yield (engineering) , reagent , hydrogen iodide , iodide , catalysis , organic chemistry , palladium , salt (chemistry) , hydrogen , medicinal chemistry , materials science , metallurgy
The addition of Grignard reagents to the 1‐phenoxycarbonyl salt of 3‐benzyloxypyridine and a catalytic amount of cuprous iodide afforded 4‐alkyl‐3‐benzyloxy‐1‐phenoxycarbonyl‐1,4‐dihydropyridines in good yield. The crude dihydropyridines were aromatized with o ‐chloranil to give 4‐alkyl‐3‐benzyloxypyridines, which were debenzylated with hydrogen and 10% palladium on carbon to provide 4‐alkyl‐3‐pyridinols.