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A convenient large scale synthesis of 2,6‐dimethyl‐4‐(trimethylstannyl)pyridine
Author(s) -
Singh Baldev,
Lesher George Y.,
Pennock Patrick O.
Publication year - 1990
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.5570270661
Subject(s) - chemistry , triethylamine , pyridine , yield (engineering) , salt (chemistry) , hydrochloride , medicinal chemistry , phosphorus , organic chemistry , extraction (chemistry) , nuclear chemistry , materials science , metallurgy
Reaction of phosphorus oxychloride with 2,6‐dimethylpyridine N ‐oxide hydrochloride ( 1 ) gave a mixture of 2‐(chloromethyl)‐6‐methylpyridine ( 2 ) and 4‐chloro‐2,6‐dimethylpyridine ( 3 ). Treatment of this mixture with triethylamine converted 2 to the quaternary salt 4 which was separated by water extraction leaving 3 which was subsequently reacted with trimethylstannyl sodium to yield 2,6‐dimethyl‐4‐(trimethylstannyl)pyridine ( 6 ).