tert-Butyldimethylsilyl chloride → 2-[1-(5-Tert-butyldimethylsilyloxy-3-(naphth-2-ylmethoxy)phenyl)-1-methoxypropyl]thiazole

Participants

Reaction Steps

Ethyl 5-hydroxy-3-(naphth-2-ylmethoxy)benzoate, obtained from ethyl 3,5-dihydroxybenzoate and 2-bromomethylnaphthalene, was reacted with tert-butyldimethylsilyl chloride using the conditions described in the 1st paragraph of the portion of Example 6 which is concerned with the preparation of starting materials and the product so obtained was reacted in turn with thiazol-2-yl-lithium and ethylmagnesium iodide following the procedures described in the portion of Example 3 which is concerned with the preparation of starting materials. There was thus obtained the required starting material in 49% yield (from ethyl 5-hydroxy-3-(naphth-2-ylmethoxy)benzoate) as an oil. This starting material was methylated using the procedure described in Example 3 to give 2-[1-(5-tert-butyldimethylsilyloxy-3-(naphth-2-ylmethoxy)phenyl)-1-methoxypropyl]thiazole as an oil, in 42% yield.

Provenance & Evidence