2-Bromopyridine → HCID 21187637, compound

Participants

Reaction Conditions

Reaction Steps

2-Bromopyridine (1.40 g, 8.86 mmol, 1 eq) was dissolved in diethyl ether (30 mL) at room temperature under nitrogen then cooled to −70° C. Added 1.6M n-butyllithium (5.54 mL, 8.86 mmol, 1 eq) dropwise via an addition funnel. Stirred at −70° C. for 1 hour then added 1,4-cyclohexanedione-mono-ethylene ketal (1.52 g, 9.57 mmol, 1.1 eq) as a diethyl ether (30 mL) solution, dropwise via an addition funnel. Stirred at 0° C. for 1 hour. Quenched with saturated ammonium chloride (25 mL). Separated the 2 layers. The aqueous layer was extracted 2 times more with methylene chloride. The organic layers were combined, dried (sodium sulfate) and stripped to give an oil. Purified over silica gel in 9:1 to 1:1 hexanes/ethyl acetate to give 8-(2-pyridinyl)-1,4-dioxaspiro[4.5]decan-8-ol (2.70 g) of an amber oil. MS found: (M+H)+=236.1

Provenance & Evidence