Benzyl Alcohol → HCID 59184824, compound

Participants

Reaction Steps

To a stirred solution of 4-(tert-butyl-diphenyl-silanyloxymethyl)-2,6-difluoro-pyridine (1.917 g, 5 mmol) and benzyl alcohol (543 μl, 5.25 mmol) in THF (20 ml) cooled in a dry ice-acetone bath (−50° C.) under nitrogen, was added 60% sodium hydride (240 mg, 6 mmol). The mixture was then slowly warmed up to room temperature during 2 hr. The mixture was diluted with ether, washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was then dissolved in THF (5 ml) and stirred with 1M tetrabutylammonium fluoride in THF (5.5 ml, 5.5 mmol) at room temperature for 1 hr. The mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether:hexane (1:3)) to afford 856 mg (73% for two steps) of (2-benzyloxy-6-fluoro-pyridin-4-yl)-methanol as a colorless oil. 1H NMR (200 MHz, CDCl3) δ 1.99 (1H, br. s), 4.68 (2H, s), 5.32 (2H, s), 6.48 (1H, s), 6.64 (1H, s), 7.30-7.45 (5H, m).

Provenance & Evidence