Diisobutylaluminum hydride → 3-Pyridinemethanol, 5-methyl-6-(trifluoromethyl)-

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-methyl-6-(trifluoromethyl)-3-pyridinecarboxylate (552 mg, 2.52 mmol) in DCM (30 ml) stirred under N2 at 0° C. was added a solution of DIBAL-H (1.5 M solution in toluene, 5.04 ml, 7.56 mmol) dropwise. The reaction mixture was stirred at 0° C. for 2 h and at room temperature overnight. The reaction mixture was diluted with MeOH and concentrated under reduced pressure. The residue was treated with a 1N HCl solution and extracted twice with EtOAc. The combined organic phases were dried over anhydrous Na2SO4 and concentrated under reduced. Purification by flash chromatography using a 10 g silica gel cartridge, and mixtures of DCM and MeOH as eluent afforded [5-methyl-6-(trifluoromethyl)-3-pyridinyl]methanol (297 mg, 54%).

Provenance & Evidence