Reaction Steps
Methacryloylchloride 90%, 0.52 ml, 4.8 mmol) was added dropwise To a stirred solution of 6-(2',5'-dimethoxy-4-stilbenoxy)hexanol (14) (1.54 g, 4.32 mmol) and dry trimethylamine (0.76 ml, 5.5 mmol) in dry tetrahydrofuran (25 ml) under argon. The reaction mixture was stirred at 60° C. for 23 h. Ether (200 ml) and water (100 ml) were added. The organic layer was washed with water (3×100 ml), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography over silica (dichloromethane/hexane; 4:1 to 1:0) to yield (15) (1.48 g, 81 %] as an oil; δH (CDCl3) 1.48 (4 H, m, CH2), 1.70 (2 H, m, CH2), 1.80 (2 H, m, CH2), 1.95 (3 H, m, CH3), 3.81 (3 H, s, OCH3), 3.83 (3 H, s, OCH3), 3.96 (2 H, J=6.4 Hz, CCH2), 4.16 (2 H, t, J=6.6 Hz, OCH2), 5.55 (1 H, m, HA), 6.10 (1 H, m, HB), 6.76 (1 H, dd, JH4',H3' =8.2 Hz, JH6',H4' =2.9 Hz, H4'), 6.82 (1 H, d, JH4',H3' =8.2 Hz, H3'), 6.87 and 7.46 (4 H, AA'BB', H2, H3, H5, and H6), 7.04 (1 H, d, J=16.5 Hz,. vinytic H), 7.13 (1 H, d, JH4',H6' =2.9 Hz, H6') and 7.32 (1 H, d, J=16.4 Hz, vinylic H); δc (CDCl3) 18.3, 25.69, 25.74, 28.5, 29.1, 53.4, 55.7, 56.2, 64.6, 67.7, 111.3, 112.2, 113.1, 114.5, 120.9, 125.2, 127.5, 127.7, 128.8, 130.4, 136.4, 151.2, 153.7, 158.6 and 167.4.
