反应详情

Phosphonium bromide 6 (3.67 g, 5.13 mmol) was dissolved in DCM at 0° C. Sodium hydride (60% dispersion in mineral oil, 0.41 g, 10.2 mmol) was added and the mixture turned orange. Next, 3-iodo-4,5-dimethoxybenzaldehyde (1 g, 3.42 mmol) was added and stirring was continued for 21 hrs. The reaction was terminated by adding water (50 mL) and extracted with DCM (3×50 mL), which was dried, filtered and concentrated. The oil obtained was subjected to flash chromatography on silica gel with the eluent 0–3% ethyl acetate in hexane to afford Z-stilbene 10a (0.86 g, 39%) which crystallized as a colorless solid from hexane: mp 122–124° C.: 1H-NMR (300 MHz, CDCl3) δ 1.07 (s, 9 H), 3.45 (s, 3 H), 3.55 (s, 3 H), 3.79 (s, 3 H), 6.21 (d, 1 H, J=12 Hz), 6.31 (d, 1 H, J=12 Hz), 6.59 (d, 1 H, J=7.8 Hz), 6.72 (s, 2 H), 6.77 (dd, 1 H, J=7.8, 1.5 Hz), 7.19 (d, 1 H, J=1.8 Hz), 7.40–7.20 (m, 6H), 7.64 (d, 4H, J=7.5 Hz); 13C-NMR (75 MHz, CDCl3) δ 19.68, 26.62, 55.05, 55.56, 60.33, 91.94, 111.72, 113.09, 120.78, 122.43, 126.73, 127.33, 129.32, 130.28, 130.93, 133.54, 135.17, 144.70, 149.82, 151.82; HRMS calcd for C33H36IO4Si 651.1428 [M+H]+, found 651.1474; Anal. calcd for C33H35I04Si C, 60.92; H, 5.45. Found, C, 60.79; H, 5.67%.

1. customThe reaction was terminated
2. additionby adding water (50 mL)
3. extractionextracted with DCM (3×50 mL), which
4. customwas dried
5. filtrationfiltered
6. concentrationconcentrated
7. customThe oil obtained