Iodoethane → 4-Chloro-2-propylpyridine

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To a solution of LDA (0.13 moles) in THF/hexanes (40 mL/40 mL) at −60° C. under argon was added a solution of 4-chloro-2-picoline (15 g) in THF (250 mL) over 20 min. After a further 30 min at −60° C. iodoethane (10.4 mL) in THF (60 mL) was added over 20 min, the reaction stirred at −60° C. for 1.5 h and then allowed to warm to −30° C. The mixture was poured into brine and extracted with dichloromethane. After drying (MgSO4) and purification by chromatography eluting with dichloromethane in petroleum ether (70-100%) followed by dichloromethane containing methanol (0 to 5%) the title compound was obtained as a brown oil (12.35 g). 1H NMR δ (CDCl3) 0.97 (3H, t), 1.75 (2H, m), 2.75 (2H, t), 7.12 (1H, m), 7.16 (1H, d), 8.42 (1H, d).

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