3,5-Dichloro-4-pyridinecarboxaldehyde → (3,5-Dichloropyridin-4-yl)methanol

Participants

Reaction Steps

A solution of 3,5-dichloropyridine-4-carboxaldehyde (1.34 g, 7.6 mmol) in MeOH (10 ml) was treated with NaBH4 (0.29 g, 7.6 mmol) and stirred at room temperature for 2 h. The reaction was quenched with water (5 ml) and concentrated in vacuo. The residue was partitioned between EtOAc (20 ml) and 10% HCl (10 ml). The aqueous layer was extracted with EtOAc and the combined organic extracts, washed with 10% NaHCO3 solution, dried (MgSO4) and concentrated in vacuo to give the title compound as a white solid (1.05 g, 78%). δH (CDCl3) 8.52 (2H, s, pyr-H), 4.94 (2H, br s, CH2OH) and 2.28 (1H, br s, OH).

Provenance & Evidence