Journal
HETEROCYCLES
Volume 81, Issue 3, Pages 699-705Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-09-11869
Keywords
1,2-Dihydro-3-benzoxepin; 2-Lithio-beta-methoxystyrene; Epoxide; Hydriodic Acid; Acid Catalyzed Cyclization
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5-Substituted 1,2-dihydro-3-benzoxepins can be prepared in reasonable overall yields from a-substituted 2-bromo-beta-methoxystyrenes. Thus, the reaction of alpha-substituted 2-lithio-beta-methoxystyrenes, generated by the bromine-lithium exchange between alpha-substituted 2-bromo-beta-methoxystyrenes and butyllithium, with epoxides gives the corresponding 2(methoxyvinyl)phenethyl alcohols. These undergo cyclization with a loss of methanol on treatment with a catalytic amount of hydriodic acid to give the desired products.
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