Diisobutylaluminum hydride → (5-Chloro-6-(difluoromethoxy)pyridin-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

A cooled (−78° C.) solution of methyl 5-chloro-6-(difluoromethoxy)nicotinate (4.080 g; 17.17 mmol) in anh. toluene (110 ml) was treated dropwise with a solution of 1 M DIBAH in toluene (60.30 ml; 60.30 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 (55 ml), 1 M aq. NaOH (11 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 affording (5-chloro-6-(difluoromethoxy)pyridin-3-yl)methanol as an orange oil. LC-MS (conditions A): tR=0.62 min.; [M+H]+: 210.25 g/mol.

Provenance & Evidence