Diisobutylaluminum hydride → (5,6-Dimethylpyridin-3-yl)methanol

Participants

Reaction Steps

To a solution of methyl 5,6-dimethyl-3-pyridinecarboxylate (276 mg, 1.671 mmol) in DCM (6 ml), DIBAL-H (1.5 M solution in toluene, 3.34 ml, 5.01 mmol) was added dropwise at −78° C. under N2. The reaction mixture was allowed to warm to rt and stirred overnight. To this solution was added saturated, aqueous NaK-tartrate solution followed by DCM. The organic phase was separated, dried and concentrated to afford 175 mg of the crude material. Purification by flash chromatography using Flashmaster II, a 5 g silica gel cartridge, and mixtures of DCM/MeOH as eluent afforded 105 mg of desired compound.

Provenance & Evidence