Acetaldehyde → 2,6-Difluoro-alpha-methyl-3-pyridinemethanol

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In nitrogen atmosphere, diisopropylamine (134 mL) was dropwise added to a solution mixture of an n-butyl lithium hexane solution (2.62 M, 368 mL) and tetrahydrofuran (800 mL) at −60° C. or below. The resulting reaction solution was stirred at −60° C. for 30 min, and then a tetrahydrofuran solution (100 mL) of 2,6-difluoropyridine (100 g) was dropwise added thereto at −60° C. or below. The resulting reaction solution was stirred at the same temperature for 1 hr, and then acetoaldehyde (97.6 mL) was dropwise added thereto. Then, a 2 N hydrochloric acid aqueous solution (1000 mL) was dropwise added to the reaction solution, and further ethyl acetate (1000 mL) and toluene (1000 mL) were added thereto. The organic layer was separated and concentrated under reduced pressure to give 129 g of the title compound. The physical property values of this compound were as follows:

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