79242-31-2Relevant academic research and scientific papers
The Synthesis of 1-Haloalkyl-1,3,4,5-tetrahydro-2-benzoxepins
TenBrink, Ruth E.,McCall, John M.
, p. 821 - 824 (2007/10/02)
Short, efficient routes to several 7,8-dimethoxy-1-haloalkyl-1,3,4,5-tetrahydro-2-benzoxepins were developed.These benzoxepins were prepared by the Lewis acid catalyzed condensation of the acetals of chloropropionaldehyde or bromoacetaldehyde with 3-(3,4-dimethoxyphenyl)-1-propanol.This condensation was facilitated by methyl substitution on the propanol.In an alternate route, ethyl 3-(3,4-dimethoxyphenyl)propanoate was acylated with 3-chloropropionyl chloride.The adduct was reduced with lithium aluminum hydride.The resultant 3-propanol was dehydrated to the corresponding tetrahydrobenzoxepin.By these two general routes, 7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzoxepins were produced which were substituted by hydrogen or methyl at benzoxepin C-4 and chloroethyl or bromomethyl at benzoxepin C-1.
