Diisobutylaluminum hydride → (4-(Difluoromethoxy)pyridin-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

A cooled (−78° C.) solution of methyl 4-(difluoromethoxy)picolinate (600 mg; 2.95 mmol) in anh. toluene (12 ml) was treated dropwise with a solution of 1 M DIBAH in toluene (8.90 ml; 8.90 mmol), and the resulting mixture was further stirred at −78° C., under nitrogen, for 5 min., and then at 0° C. for 3 h. The obtained mixture was treated successively with water (50 ml), 1 M aq. NaOH (10 ml), and aq. sat. NaHCO3 (100 ml). The separated aq. layer was further extracted with Et2O (2×100 ml). The mixed organic layers were then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=1/1) afforded (4-(difluoromethoxy)pyridin-2-yl)methanol as a yellow solid. LC-MS (conditions A): tR=0.20 min.; [M+H]+: 176.17 g/mol.

Provenance & Evidence