Sodium hydride → HCID 178472477, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of ethyl 4-hydroxycyclohexanecarboxylate (20.7 g, 120.19 mmol) and 2,4-difluoronitrobenzene (19.125 g, 120.19 mmol) in DMF at 5° C. was added NaH (5.05 g, 126.2 mmol) in one portion, resulting in a slow exotherm to 10° C. The reaction was stirred at 5° C. for 1 hour then allowed to warm to ambient temperature and stirred for 24 hr. The reaction was cooled to 0° C. and quenched with water (˜400 mL). The mixture was extracted with EtOAc (3ט150 mL), the organic layers combined, washed with brine (2ט100 mL), dried (MgSO4), filtered and evaporated to an orange oil (36 g). The crude residue was purified by preparative HPLC (silica, 4:1 ethyl acetate:isohexane) to give the title compound (4.5 g, 12%) as a pale orange oil.

Provenance & Evidence