反应详情

温度

0 °C

A solution of ethyl 4-hydroxycyclohexanecarboxylate (2.0 g, 11.6 mmol) in DMF (3 ml) was added in one portion to a stirred suspension of sodium hydride (60% dispersion in mineral oil, 490 mg, 12.2 mmol) in DMF (15 mL) at 0° C. under an argon atmosphere. The mixture was stirred at 0° C. for 10 minutes and then warmed to room temperature and stirred for 20 minutes and then a solution of 1-fluoro-4-nitrobenzene (1.24 mL, 11.6 mmol) in DMF (2 mL) was added in one portion. The reaction mixture was stirred at room temperature for 2 h and then heated at 110° C. for 24 h. The solution was concentrated in vacuo to leave a residue that was taken up in EtOAc (250 mL) and water (150 mL) was added. The layers were separated and the organic layer was washed with H2O (2×100 mL) and brine (50 mL) and then dried (MgSO4) and concentrated in vacuo to leave an oil. The oil was taken up in a mixture of hot EtOAc and isohexane (1:1) and left for 20 h. Filtration, followed by concentration in vacuo of the filtrate left an oil, which was purified by column chromatography, using 10-40% EtOAc in isohexane as eluent, to give crude ethyl 4-(4-nitrophenoxy)cyclohexanecarboxylate as an off white solid that was used without further purification.

1. temperaturewarmed to room temperature
2. stirringstirred for 20 minutes
3. stirringThe reaction mixture was stirred at room temperature for 2 h
4. temperatureheated at 110° C. for 24 h
5. concentrationThe solution was concentrated in vacuo
6. customto leave a residue that
7. customThe layers were separated
8. washthe organic layer was washed with H2O (2×100 mL) and brine (50 mL)
9. dry with materialdried (MgSO4)
10. concentrationconcentrated in vacuo
11. customto leave an oil
12. waitleft for 20 h
13. filtrationFiltration
14. concentrationfollowed by concentration in vacuo of the filtrate
15. waitleft an oil, which
16. customwas purified by column chromatography