Reaction Steps
To a solution of 4.89 g (18.1 mmol) of 1-nitro-4-(4-ethoxycarbonylphenyl)-2-butanol in 24 mL of dry methylene chloride at 0° C. was added 2.1 g (18.1 mmol) of methanesulfonyl chloride followed by addition of 3.66 g (36.2 mmol) of triethylamine. The mixture was stirred at 0° C. for 20 minutes, poured into 40 mL of water, extracted with 50 mL of methylene chloride, dried over anhydrous, and concentrated under reduced pressure. The residual solid was purified by column chromatography on silica gel, eluting with 1:9 ethyl acetate:hexanes, to afford 4.1 g (90%) of 1-nitro-4-(4-ethoxycarbonylphenyl)-1-butene as a light yellow solid: IR (KBr) 3112, 2982, 1713, 1647, 1610, 1519, 1424, 1417, 1353, 1277, 1178, 1104, 1021, 954, 935, 857, 766, 706 cm-1. 1H NMR (CDCl3) δ 8.02 (2H, d, J=8.5 Hz), 7.28 (1H, dt, J=14.0 and 7.5 Hz), 7.27 (2H, d, J=8.5 Hz), 6.98 (1H, d, J=14.0 Hz), 4.39 (2H, q, J=7.0 Hz), 2.92 (2H, t, J=7.5 Hz), 2.64 (2H, q, J=8.0 Hz), 1.42 (3H, t, J=7.0 Hz); 13C NMR (CDCl3) δ 166.55, 144.90, 140.91, 140.39, 130.23, 129.27, 128.49, 61.16, 34.12, 29.89, 14.52; EIMS m/z 249 (M+), 204, 202, 163, 135, 129, 118, 107, 90, 77; HRMS calc'd for C13H15NO4 249.1001 found 249.1029.
