Cyclohexanone → HCID 10352983, compound

Participants

Reaction Conditions

Reaction Steps

According to Scheme 26 Step 1: To a stirred solution of 4-bromo-2-methoxypyridine (1 eq, 5.30 mmol, 1.00 g) in anhydrous THF (30 mL) at −78° C. under nitrogen was added dropwise a solution of butyl lithium (1.3 eq, 2.5M solution in hexane, 6.90 mmol, 2.8 mL). The reaction was then stirred at −78° C. for 2 hours. Cyclohexanone (5 eq, 27.0 mmol, 2.8 mL) was then added dropwise over 5 minutes. The reaction was stirred at −78° C. for two hours then allowed to warm to room temperature. The reaction was stirred for a further 16 hours then quenched with water. The reaction was evaporated in vacuo, redissolved in CH2Cl2 (100 mL) and washed with brine (100 mL). The organic phase was extracted, dried over MgSO4, filtered and evaporated to leave a yellow oil. The oil was purified by column chromatography (AIT Flashsmart prepacked column 25 g SiO2, pure AcOEt), yielding the title compound (4.10 mmol, 0.86 g, 78%) as a colorless oil which solidified on standing.

Provenance & Evidence