反应详情

To a solution of the alcohol (53) (0.62 g, 2.46 mmol) in DMF (4 mL) was added sodium hydride (60% dispersion in mineral oil, 0.246 g, 6.14 mmol) in a single portion and the mixture sonicated under a flow of nitrogen and then stirred at RT for 30 min. The resulting yellow suspension was cooled to 0° C. and a solution of 1-fluoro-4-nitronaphthalene (14) (0.470 g, 2.457 mmol) in DMF (2 mL) was added over 10 min. The reaction mixture was warmed to RT and glacial acetic (1.0 mL) was added. The mixture was poured onto saturated aqueous NaHCO3 solution and extracted with EtOAc. The organic layer was washed with saturated aqueous Na2CO3, solution, three times with water and twice with brine then dried (MgSO4) and evaporated in vacuo to give a yellow solid. The solid was suspended in MeOH (20 mL) and sonicated and the insoluble residue was collected by filtration and was washed with MeOH (10 mL) and then ether to afford the title compound (54) as an off white solid (0.73 g, 67%): m/z 424 (M+H)+ (ES+).

1. customthe mixture sonicated under a flow of nitrogen
2. temperatureThe resulting yellow suspension was cooled to 0° C.
3. temperatureThe reaction mixture was warmed to RT
4. extractionextracted with EtOAc
5. washThe organic layer was washed with saturated aqueous Na2CO3, solution, three times with water and twice with brine
6. dry with materialthen dried (MgSO4)
7. customevaporated in vacuo
8. customto give a yellow solid
9. customsonicated
10. filtrationthe insoluble residue was collected by filtration
11. washwas washed with MeOH (10 mL)