HCID 11189560, compound → HCID 69031670, compound

Participants

Reaction Steps

To a stirred solution of 4 (14.66 g, 34.22 mmol) in tetrahydrofuran (150 ml) was added dropwise vinylmagnesium bromide (68.44 ml, 68.44 mmol, 1.0 M solution in tetrahydrofuran) at −78° C., and the reaction mixture was stirred for 1 hour at the same temperature. The reaction mixture was quenched by saturated ammonium chloride solution and brine, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated. The resulting oil was purified by column chromatography (hexane:ethyl acetate=9:1) to give 5 (15.62 g, 100%) as a white semi-solid; 1H NMR (400 MHz, CDCl3) δ 7.43-7.22 (m, 15H), 6.16 (dd, J=17.2, 10.8 Hz, 1H), 6.01-5.93 (m, 1H), 5.42 (dd, J=17.2, 1.2 Hz, 1H), 5.27 (dd, J=10.8, 1.2 Hz, 1H), 4.99 (d, J=16.0 Hz, 1H), 4.98 (d, J=11.2 Hz, 1H), 4.54-4.47 (m, 2H), 3.33 (d, J=8.8 Hz, 1H), 3.05 (d, J=8.4 Hz, 1H), 2.54 (bs, 1H), 1.46 (s, 3H), 1.40 (s, 3H).

Provenance & Evidence