Water → (6-Fluoropyridin-3-yl)methanol

Participants

Reaction Steps

The mixture of 5-(chloromethyl)-2-fluoropyridine and 5-(dichloromethyl)-2-fluoropyridine (30.7 g, 211 mmol) was placed into a round-bottomed flask with H2O (300 mL) and K2CO3 (32.1 g, 232 mmol), which was heated to an oily suspension for 4 h. The mixture was then cooled to rt, and the layers were separated. The aqueous layer was washed with EtOAc (2×50 mL). The combined organic layers were then washed with H2O (3×100 mL), dried over MgSO4, filtered, and concentrated. This mixture was purified by column chromatography (6:1 hexane:EtOAc) to yield (6-fluoropyridin-3-yl)methanol and 6-((6-fluoropyridin-3-yl)methoxy)nicotinaldehyde.

Provenance & Evidence