NEW ORGANOTIN SYNTHONS PROVIDING α-ALKOXYORGANOLITHIUM REAGENTS

Article abstract of DOI:10.1016/S0022-328X(00)85670-3

Diethoxymethyltributyltin was obtained in high yield from the reaction of tributylstannylmagnesium chloride with diethylphenylorthoformate.It reacted readily with acetyl chloride to give chloroethoxymethyltributyltin, which was easily transformed to ethoxymethyltributyltin by reduction with tributyltin hydride.Diethoxymethyltributyltin, a masked aldehyde anionic equivalent, was metallated with butyllithium, and the resulting new organolithium reagent was trapped with benzyl bromide, benzaldehyde, and cyclohexenone.