Methyl 6-methoxypyridine-3-carboxylate → (2-Methoxypyridin-4-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a 0° C. THF (70 mL) solution of methyl 6-methoxynicotinate (6.0 g, 36 mmol) was added 36 mL of 1M LAH/THF. The reaction, after stirring at 20° C. for two hours, was quenched with aq. NH4Cl, diluted with aq. HCl until all salts dissolved, and extracted with EtOAc (3×) after adjusting the pH to 5. The crude 4-hydroxymethyl-2-methoxypyridine (1.75 g), obtained after drying and concentration of the EtOAc layers, was converted to 4-methoxy-3-pyridinylcarboxaldehyde following the procedure described in step A of Example 123. The title compound was prepared from 4-methoxy-3-pyridinylcarboxaldehyde following the procedure described in step A of Example 119.

Provenance & Evidence