Tetrabutylammonium Fluoride → (4-Fluoro-phenyl)-(5-hydroxymethyl-pyridin-3-yl)-methanone

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Reaction Steps

To a solution of [5-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-3-yl]-(4-fluoro-phenyl)-methanone (1H) (1.7 g, 4.9 mmol) in 20 mL of tetrahydrofuran (THF) at 0° C., is added tetra-butyl-ammonium-fluoride (9.8 mL, 9.9 mmol, 1M in THF) slowly. After being stirred at room temperature for 1 hour, the reaction solution is quenched by addition of 5 mL of water and extracted with 3×10 mL of EtOAc. After concentration, the crude product is purified by chromatography (heptane 80%, EtOAc 20%) to give (4-fluoro-phenyl)-(5-hydroxymethyl-pyridin-3-yl)-methanone (1I) (0.97 g, yield 86%) as white solid. MS (ESI) m/e 232 (M+H+).

Provenance & Evidence