Sodium hydride → HCID 66764424, compound

Participants

Reaction Conditions

Reaction Steps

NaH (0.250 g, 6.25 mmol) was added to a mixture of ethyl 4-hydroxycyclohexanoate (0.916 ml, 5.68 mmol), and 5-bromo-2-fluoropyridine (0.585 mL, 5.68 mmol) in DMF (15 mL) at room temperature under an argon atmosphere. The reaction mixture was heated to 80° C. for 2.5 hours. Upon cooling, the reaction mixture was diluted with saturated NaHCO3 (50 mL), extracted with ethyl acetate (50 mL) and diethyl ether (50 mL), washed with water, brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (hexanes/ethyl acetate) to afford ethyl 4-[(5-bromopyridin-2-yl)oxy]cyclohexanecarboxylate. MS ESI calc'd for C14H19BrNO3 [M+H]+ 328 and 330. found 328 and 330.

Provenance & Evidence