Tributylvinyltin → HCID 67170307, compound

Participants

Reaction Conditions

Reaction Steps

5-(7-Bromo-4,5-dihydronaphtho[1,2-c]isoxazol-3-yl)-2-isopropoxybenzonitrile (Preparation 15B, 0.15 g, 0.367 mmol) dissolved in dioxane (3 mL) was transferred to a 15 mL sealed tube. Tributyl(vinyl)stannane (0.118 mL, 0.403 mmol) was added followed by lithium chloride (0.047 g, 1.100 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.042 g, 0.037 mmol). The contents were purged with nitrogen gas for 5 min., immersed in an oil bath, and heated at 100° C. for 14 h. The reaction mixture was concentrated and to the red-brown oil was added ethyl acetate (10 mL). The contents were sonicated for 5 min. and filtered. The filter cake was washed with ethyl acetate (2×5 mL). The filtrate was concentrated under reduced pressure and the resulting oil was subjected to silica gel column chromatography (hexane/ethyl acetate). Fractions corresponding to the product were collected and concentrated to yield 2-isopropoxy-5-(7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazol-3-yl)benzonitrile (0.088 g, 0.247 mmol, 67% yield) as a pale yellow solid. LC/MS M+1=357.1.

Provenance & Evidence