Tributylvinyltin → HCID 67168875, compound

Participants

Reaction Steps

To a solution of 8,8-dimethyl-5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (Preparation 1B, 0.443 g, 1.37 mmol) in dioxane (2.5 mL) in a sealed tube was added sequentially tributyl(vinyl)stannane (0.444 mL, 1.51 mmol) and lithium chloride (0.175 g, 4.12 mmol). The mixture was degassed under reduced pressure and charged with nitrogen (2×). To the mixture was added tetrakis(triphenylphosphine) palladium(0) (0.159 g, 0.137 mmol), and the mixture was stirred under a strong stream of nitrogen for 5 min. The reaction mixture was sealed, immersed in an oil bath at 100° C., and stirred at room temperature overnight. The reaction mixture was filtered under reduced pressure, and the solid was rinsed with ethyl acetate (˜50 mL total). The filtrate was concentrated under reduced pressure, and the resulting residue was diluted with ether (˜25 mL). The resulting solid was removed by vacuum filtration and rinsed with ether (˜25 mL). The filtrate was concentrated under reduced pressure and purified by flash silica gel chromatography using a mixture of ethyl acetate in hexane (5%-10%) to give 4,4-dimethyl-6-vinyl-3,4-dihydronaphthalen-1(2H)-one (0.201 g, 1.00 mmol, 73. % yield) as a colorless oil. The product had an HPLC ret. time=2.55 min. (condition A); LC/MS M+1=200.9.

Provenance & Evidence