Tributylvinyltin → 3-(4-Propylphenyl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole

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Reaction Steps

To a mixture of 3-(4-propylphenyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate (Preparation 11A, 160 mg, 0.272 mmol), anhydrous lithium chloride (34.6 mg, 0.817 mmol), tributyl(vinyl)tin (0.120 mL, 0.409 mmol), and anhydrous dioxane (1 mL) was bubbled nitrogen gas for 3 min before Pd(Ph3P)4 (62.9 mg, 0.054 mmol) was added. The reaction mixture was purged with nitrogen gas for an additional 3 min, stirred for 1 h at room temperature, and then at 110° C. for 4 h. The reaction mixture was cooled and treated with saturated aqueous sodium bicarbonate solution (1.5 mL). The biphasic mixture was extracted with ethyl acetate (2×2 mL). The combined ethyl acetate extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was dissolved in dichloromethane and filtered through a pad of silica gel and rinsed with dichloromethane. The filtrate was concentrated to give 3-(4-propylphenyl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole (74 mg, 0.235 mmol, 86% yield) LC/MS M+1=316.17.

Provenance & Evidence