反应详情

温度

72 °C

A solution of 85C (2.2 g, 5.5 mmol) in CH2Cl2 (200 mL) was degassed by bubbling argon for 8 min. To this solution was added Grubb's catalyst (2nd generation, 380 mg, 0.45 mmol). The mixture was heated at 72° C. for 5.0 h. After removal of solvent, the crude was purified by silica gel column chromatography using gradient EtOAc in hexanes to give 85D as a major product (1.66 g, 82% yield): 1H NMR (400 MHz, CDCl3) δ ppm 0.71-0.80 (m, 2H) 1.15-1.19 (s, 9H) 1.19-1.25 (m, 2H) 2.14-2.22 (m, 1H) 3.78 (dt, J=14.50, 2.64 Hz, 1H) 4.69 (dd, J=14.50, 2.64 Hz, 1H) 5.73 (dd, J=6.15, 2.20 Hz, 1H) 5.85 (dd, J=5.05, 2.42 Hz, 1H) 5.88 (ddd, J=4.06, 2.20, 2.09 Hz, 1H) 7.69 (d, J=8.79 Hz, 1H) 8.06 (dd, J=8.57, 2.42 Hz, 1H) 8.19 (d, J=2.20 Hz, 1H), LC-MS 367 (M+H). 85E was obtained as a minor product (0.31 g, 14% yield): 1H NMR (400 MHz, CDCl3) δ ppm 0.65-0.73 (m, 1H) 0.73-0.82 (m, 1H) 1.01 (s, 9H) 1.17-1.26 (m, 2H) 2.15-2.24 (m, J=7.96, 3.90, 3.74, 3.74 Hz, 1H) 4.36-4.43 (m, 1H) 4.51-4.58 (m, 1H) 5.82 (dd, J=6.15, 2.20 Hz, 1H) 5.87 (d, J=1.76 Hz, 1H) 5.90 (dd, J=5.05, 2.86 Hz, 2H) 7.66 (d, J=8.79 Hz, 1H) 8.06 (dd, J=8.57, 2.42 Hz, 1H) 8.13 (d, J=2.20 Hz, 1H), LC-MS 367 (M+H).

1. customby bubbling argon for 8 min
2. customAfter removal of solvent
3. customthe crude was purified by silica gel column chromatography