Tributylvinyltin → 2-vinyl-7,8-dihydroquinolin-5(6H)-one

Participants

Reaction Steps

To a solution of 5-oxo-5,6,7,8-tetrahydroquinolin-2-yl trifluoromethanesulfonate (Preparation 54B, 2.21 g, 7.49 mmol) in dioxane (12 mL) in a sealed tube was added sequentially tributyl(vinyl)stannane (2.418 mL, 8.23 mmol) and lithium chloride (0.952 g, 22.46 mmol). The mixture was degassed under reduced pressure and charged with nitrogen (3×). To the mixture was added tetrakis(triphenylphosphine)palladium(0) (0.865 g, 0.749 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 overnight. The reaction mixture was filtered and the solid was rinsed with ethyl acetate (150 mL). The filtrate was concentrated under reduced pressure, and the resulting residue was diluted with ether (150 mL). The resulting solid was removed by vacuum filtration and rinsed with ether (150 mL). The filtrate was concentrated under reduced pressure and purified by flash silica gel chromatography using a mixture of ethyl acetate in hexane (5%-12.5%-20%) to give 2-vinyl-7,8-dihydroquinolin-5(6H)-one (1.09 g, 6.29 mmol, 84% yield) as a pale yellow solid. The compound had an HPLC ret. time=0.738 min. (condition A); LC/MS M+1=273.8; 1H NMR (500 MHz, CDCl3) δ ppm 2.21 (quin, 2H), 2.67-2.73 (m, 2H), 3.15 (t, J=6.10 Hz, 2H), 5.65 (d, J=10.82 Hz, 1H), 6.35 (d, J=17.48 Hz, 1H), 6.86 (dd, J=17.48, 10.54 Hz, 1H), 7.34 (d, J=8.05 Hz, 1H), and 8.25 (d, J=8.05 Hz, 1H).

Provenance & Evidence