Tributylvinyltin → HCID 67171363, compound

Participants

Reaction Conditions

Reaction Steps

To 7-bromo-3-(4-propylphenyl)-4,5-dihydronaphtho[2,1-d]isoxazole (Preparation 20C, 0.32 g, 0.869 mmol) in dioxane (3 mL) were added sequentially lithium chloride (0.111 g, 2.61 mmol) and tributyl(vinyl)stannane (0.251 mL, 0.869 mmol). The reaction mixture was purged with nitrogen gas for 3 min. Tetrakis(triphenylphosphine) palladium(0) (0.100 g, 0.087 mmol) was added and the resulting yellow solution was purged with nitrogen gas for 2 min., and heated at 100° C. for 2 h. The reaction mixture was concentrated under reduced pressure and the residue was subjected to silica gel column chromatography using hexane/ethyl acetate. Fractions corresponding to the desired product were collected and concentrated to yield 3-(4-propylphenyl)-7-vinyl-4,5-dihydronaphtho[2,1-d]isoxazole (0.205 g, 0.650 mmol, 74.8% yield) as a pale yellow solid. LCMS M+1=316.2.

Provenance & Evidence