Methyl 4-(trifluoromethyl)nicotinate → (4-(Trifluoromethyl)pyridin-3-yl)methanol

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To a stirred suspension of LAH (0.64 g, 17.0 mmol) in THF (30 mL) at -78° C. was added dropwise methyl 4-trifluoromethylnicotinate (1.74 g, 8.48 mmol) in THF (20 mL). The mixture was stirred for 1 h then carefully quenched with aqueous NaHCO3 (80 mL) and extracted with CH2Cl2 (3×100 mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo to give 3-hydroxymethyl-4-trifluoromethylpyridine as an oil (TLC: Rf = 0.35 (1:1 hexane:EtOAc)).

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