Diisobutylaluminum hydride → (6-(Difluoromethoxy)pyridin-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

A cooled (−78° C.) solution of methyl 6-(difluoromethoxy)nicotinate (4.700 g; 23.13 mmol) in anh. toluene (130 ml) was treated dropwise with a solution of 1 M DIBAH in toluene (69.40 ml; 69.40 mmol), and the resulting mixture was further stirred at −78° C., under nitrogen, for 5 min., and then at 0° C. for 1.5 h. The obtained mixture was then treated successively with water (55 ml), 1 M aq. NaOH (12 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 (6-(difluoromethoxy)pyridin-3-yl)methanol as a yellow oil (3.758 g; 93%). LC-MS (conditions D): tR=0.71 min.; no ionisation.

Provenance & Evidence