Hydrochloric Acid → HCID 67530309, compound

Participants

Reaction Steps

A stirred solution of 3.0 grams (0.0081 mole) of 1-{[2-(7-methoxy-6-methyl(3,4-dihydronaphthyl))imidazolyl]methoxy}-3,3-dimethyl-3-silabutane (xii), 5 mL of aqueous 3N hydrochloric acid, and 25 mL (0.025 mole) of tetrabutylammonium fluoride (1.0M in THF) was warmed to 50° C. where it stirred for about two hours. After this time, analysis of the reaction mixture using thin layer chromatography indicated that the reaction had not gone to completion. The reaction mixture was concentrated under reduced pressure to a residue and 15 mL of concentrated hydrochloric acid was added. Upon completion of addition, the reaction mixture was stirred at ambient temperature during an 18 hour period. After this time, the reaction mixture was poured into a mixture of aqueous 50% sodium hydroxide and ice. The mixture was stirred until the ice melted, and a solid was collected by filtration. The solid was washed with ethyl acetate and dried, yielding 1.2 grams of the subject compound, mp 197-229° C. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence