Diethyl Ether → ST51008769

참여 물질

반응 단계

A two necked round-bottom flask (250 mL) containing a stir bar fitted with a reflux condenser was evacuated and purged with nitrogen gas. Dry ether (50 mL) and 2-bromothiophene (0.0191 mol, 3.06 g) was added to the flask followed by the slow addition of n-BuLi (0.0229 mol, 9.17 mL) via a syringe pump. The reaction mixture was stirred at room temperature for 30 min to 40 min and then 4-methylquinoline (0.0191 mol, 2.72 g) was slowly added. The reaction mixture was refluxed for an additional 2 to 3 hr. The reaction mixture was then cooled to room temperature and diluted with an aqueous brine solution and extracted with ether (3×30 mL). The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography using hexanes/CH2Cl2 as eluent to afford 2.77 g of 4-methyl-(2-thiophenyl)quinoline (65% yield).

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