Tributylvinyltin → HCID 67170771, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 8-methyl-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl trifluoromethanesulfonate (Preparation 64D, 0.120 g, 0.220 mmol) and lithium chloride (0.014 mL, 0.661 mmol) in dioxane (15 mL) was degassed with nitrogen for 15 minutes. Tributyl(vinyl)stannane (0.077 g, 0.242 mmol) was added followed by the addition of tetrakis(triphenylphosphine) palladium(0) (0.025 g, 0.022 mmol) at room temperature. The resulting reaction mixture was heated at 100° C. overnight. The reaction mixture was cooled to room temperature and filtered. The brownish residue was washed with ethyl acetate (3×10 mL), and the combined filtrates were concentrated under reduce pressure. The residue was chromatographed on silica gel eluting with a mixture of 10% ethyl acetate and 90% hexane to yield 8-methyl-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole (0.088 g, 0.137 mmol, 62% yield) as a tan viscous liquid. The product had an HPLC ret. time=4.58 min (condition B). LC/MS M+1=423.30.

Provenance & Evidence