Hexane → HCID 57803252, compound

Participants

Reaction Steps

1.6M n-Hexane solution of n-butyl lithium (66 ml) was added dropwise to a solution of 2,5-dibromopyridine (23.9 g) in toluene (420 ml) at −78° C., and stirred at the same temperature for an hour. Next, a solution of 1,4-cyclohexanedione monoethyleneketal (15 g) in dichloromethane (60 ml) was added dropwise, and the reaction solution was warmed up to room temperature over 7 hours. After completion of the reaction, a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate three times. The organic solution was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) and recrystallized from n-hexane/diethyl ether to give 8-(5-bromopyridin-2-yl)-1,4-dioxaspiro[4,5]decan-8-ol (16.2 g) as a white solid.

Provenance & Evidence