反应详情

温度

-78 °C

Methyl triphenylphosphonium bromide was suspended in 15 mL of dry THF under argon and stirred at −78° C. Butyllithium (1.6M, 0.42 mL) was added dropwise over 2 min. and then the reaction mixture was allowed to stir at 0° C. for 1.5 hours. The solution was cooled again to −78° C., treated dropwise with a solution of 2,6-diisopropyl-4-(4-fluorophenyl)-5-pentyl-3-pyridinecarboxaldehyde (Example 114, Step A) in 5 mL of dry THF, and then stirred at 0° C. for 2.5 hours. The reaction was quenched with water (10 mL) and the THF evaporated in vacuo. Diethyl ether was added and the mixture was washed with water (2×20 mL), brine (1×20 mL), and dried with MgSO4. Filtration, concentration and flash chromatography (30% CH2Cl2/hexanes) yielded a solid (0.132 g, 0.37 mmol, 66%). 1H NMR (300 MHz, CDCl3) δ 7.08 (m, J=1.1 Hz, 4 H), 6.34, 6.28 (d, J=11.4 Hz, J=11.4 Hz, 1 H), 5.19 (d, J=1.8 Hz, 1 H), 4.96 (d, J=1.8 Hz, 1 H), 3.39 (septet, J=6.6 Hz, 1 H), 3.24 (septet, J=6.6 Hz, 1 H), 2.30 (t, J=5.2 Hz, 2 H), 1.20 (m, J=2.2 Hz, 18 H), 0.979 (t, J=6.0 Hz, 3 H). FAB-MS: calcd for (C24H32FN) 353, found 354 (M+H). Anal. Calcd for C24H32FN: C, 81.54; H, 9.12; N, 3.96; F, 5.37. Found: C, 81.46; H, 9.06; N, 3.78; F, 5.59. mp 44-46° C. Rf=0.7 (30% CH2Cl2/hexanes).

1. stirringto stir at 0° C. for 1.5 hours
2. temperatureThe solution was cooled again to −78° C.
3. stirringstirred at 0° C. for 2.5 hours
4. customThe reaction was quenched with water (10 mL)
5. customthe THF evaporated in vacuo
6. additionDiethyl ether was added
7. washthe mixture was washed with water (2×20 mL), brine (1×20 mL)
8. dry with materialdried with MgSO4
9. filtrationFiltration, concentration and flash chromatography (30% CH2Cl2/hexanes)