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0 °C

Sodium hydride (60% dispersion in mineral oil, 4.39 g, 109.7 mmol) was added in portions over 1 min to a stirred solution of ethyl 4-hydroxycyclohexanecarboxylate (18 g, 104.5 mmol) and 1-fluoro-4-nitrobenzene (11.1 mL, 109.7 mmol) in DMF (200 mL) at 0° C. under a nitrogen atmosphere. The reaction mixture was stirred at 0° C. for 5 mins and then warmed to ambient temperature and stirred for 2 h. Water (750 mL) and EtOAc (300 mL) were then added and the layers were separated. The aqueous layer was extracted with EtOAc (2×300 mL) and the combined organic layers were washed with brine (100 mL), dried (MgSO4) and concentrated in vacuo to leave a residue. The crude residue was purified by column chromatography, using a gradient of 10-40% EtOAc in isohexane as eluent, to give the title compound as a yellow oil (6.95 g, 23.7 mmol, 23%).

1. temperaturewarmed to ambient temperature
2. stirringstirred for 2 h
3. customthe layers were separated
4. extractionThe aqueous layer was extracted with EtOAc (2×300 mL)
5. washthe combined organic layers were washed with brine (100 mL)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo
8. customto leave a residue
9. customThe crude residue was purified by column chromatography