反应详情

To a solution of ethyl 2-(diethoxyphosphoryl)acetate (0.714 mL, 3.57 mmol) in 10 mL of THF at 0° C. was added 1 M potassium tert-butoxide in THF (3.57 mL, 3.57 mmol) dropwise, and the mixture was stirred for 15 mins at the same temperature. Then a solution of 1-(4-fluorophenyl)cyclohexanecarbaldehyde (Intermediate I-7A, 368 mg, 1.784 mmol) in 3 mL of THF was added dropwise, and the mixture was stirred at room temperature for 18 hrs. The reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate extract was washed with brine, dried over sodium sulfate and evaporated to give an oily residue which was purified by Combiflash (80 g silica gel) eluting with hexane followed by 5:95 EtOAc-hexane to give the desired (E)-ethyl 3-(1-(4-fluorophenyl)cyclohexyl)acrylate (453 mg, 92% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.28 (2H, dd, J=9.02, 5.28 Hz), 7.01 (2H, t, J=8.80 Hz), 6.95 (1H, d, J=16.07 Hz), 5.60 (1H, d, J=16.07 Hz), 4.16 (2H, q, J=7.26 Hz), 1.99-2.08 (2H, m), 1.85-1.94 (2H, m), 1.39-1.62 (6H, m), 1.27 (3H, t, J=7.15 Hz).

1. stirringthe mixture was stirred at room temperature for 18 hrs
2. customThe reaction mixture was partitioned between ethyl acetate and water
3. extractionThe ethyl acetate extract
4. washwas washed with brine
5. dry with materialdried over sodium sulfate
6. customevaporated
7. customto give an oily residue which
8. customwas purified by Combiflash (80 g silica gel)
9. washeluting with hexane