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Facile addition of methyl lithium to a 4‐vinylpyridine system
Author(s) -
Miller David
Publication year - 1984
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.5570210420
Subject(s) - chemistry , lithium (medication) , hydrochloric acid , medicinal chemistry , organic chemistry , medicine , endocrinology
The rapid addition of methyl lithium to the 4‐vinylpyridine system present in 4‐{2,6‐dihydroxy‐4‐(3‐methyl‐2‐octyl)phenyl}‐2‐methyl‐4‐(4‐pyridyl)but‐3‐en‐2‐ol ( 2 ) is reported. The α and β‐4‐{2,6‐dihydroxy‐4‐(3‐methyl‐2‐octyl)phenyl}‐2,3‐dimethyl‐4‐(4‐pyridyl)butan‐2‐ols 4 and 5 formed, are cyclised by heating with 5 N hydrochloric acid to trans and cis ‐3,4‐dihydro‐5‐hydroxy‐7‐(3‐methyl‐2‐octyl)‐4‐(4‐pyridyl)‐2,2,3‐trimethyl‐2 H ‐1‐benzopyran 6 and 7 respectively.