Methanol → Benzofuran-5-yl(pyridin-2-yl)methanol

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Under argon at −78° C., a mixture of 2-bromopyridine (1.11 g, 7.05 mmol) in THF (30 mL) was dropwise treated with n-BuLi (1.05 equiv. 2.7 mL of 2.5M BuLi in hexanes) over a period of 10 min, and stirred for 10 min. The resulting brown solution was treated dropwise with a solution of benzofuran-5-carbaldehyde (0.937 g, 6.41 mmol) in THF (10 mL) and continued to stir for 15 min at −78° C. The mixture was treated with MeOH (3 mL), followed by H2O (20 mL) and warmed to 4° C. The mixture was treated with EtOAc, the layers separated, and the aqueous layer extracted 1× with EtOAc. The combined organic layers were dried over MgSO4 and evaporated, which resulted in a dark yellow oil which was used without further purification.

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