Water → HCID 178472476, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60% dispersion in mineral oil, 5.05 g, 126 mmol) was added in one portion to a stirred solution of ethyl 4-hydroxycyclohexanecarboxylate (20.7 g, 120 mmol) and 2,4-difluoronitrobenzene (19.1 g, 120.2 mmol) in DMA (100 mL) at 4° C. and the mixture was stirred at 4° C. for 1 h and then the reaction mixture was warmed to ambient temperature and stirred for 24 h. The reaction mixture was cooled to 0° C. and then water and ethyl acetate were added. The layers were separated and the organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo to leave a yellow oil. The oil was purified by column chromatography, using a gradient of 20-50% ethyl acetate in isohexane as eluent, to give the title compound as a pale yellow solid (4.1 g, 11%).

Provenance & Evidence