5-Butyl-2-methylpyridine → HCID 53825401, compound

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Reaction Steps

46 ml of a 2.2 molar solution of phenyllithium in cyclohexane/diethyl ether (7:3) are added with ice cooling to a solution of 14.9 g of 5-butyl-2-picoline in 50 ml of diethyl ether. After 1 hour of stirring, 15.9 g of 4-ethoxybenzyl chloride in 50 ml of diethyl ether are then added at room temperature, and the ether starts to boil. The reaction mixture is poured onto ice after 1 hour, and the organic phase is worked up. Separation by column chromatography (silica gel, toluene) and recrystallization gives 2-(p-ethoxyphenylethyl)-5-butylpyridine.

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