Methyl4,6-dichloronicotinate → (4,6-Dichloropyridin-3-yl)methanol

Participants

Reaction Steps

To lithium aluminum hydride (2.4 g, 64 mmol) and aluminum chloride (17 g, 128 mmol) in Et2O (200 mL) at 0° C. was added a solution of methyl 4,6-dichloronicotinate (13.1 g, 64 mmol) in Et2O (100 mL) dropwise with stirring. The resulting solution was heated at reflux for one hour. The reaction mixture was quenched with 100 mL of H2O/ice. The resulting solution was extracted with EtOAc (2×500 mL). The organic layers were combined, dried over Na2SO4 and concentrated in vacuo to afford 4.5 g (43%) of (4,6-dichloropyridin-3-yl)methanol.

Provenance & Evidence