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

Temperature

0 °C

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%).

1. concentrationconcentrated under reduced pressure
2. additionThe residue was treated with a 1N HCl solution
3. extractionextracted twice with EtOAc
4. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
5. concentrationconcentrated under reduced
6. customPurification by flash chromatography

ORD record

ord-65daa97868ad45abbd460f6fa856b4d3

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08097628B2