3-(5-(Tert-butyl)-2-((2-methoxyethoxy)methoxy)phenyl)-6-(trifluoromethyl)pyridazine → 4-(Tert-butyl)-2-(6-(trifluoromethyl)pyridazin-3-yl)phenol

Participants

Reaction Steps

A solution of 3-(5-(tert-butyl)-2-((2-methoxyethoxy)methoxy)phenyl)-6-(trifluoromethyl)pyridazine (0.452 g, 1.18 mmol) in methanol (50 mL) and 1.0M aqueous hydrochloric acid (25 mL) was stirred at 60° C. for 5 hours. The cooled reaction mixture was then concentrated under reduced pressure to remove methanol. The resulting aqueous suspension was partitioned between ethyl acetate (80 mL) and saturated aqueous sodium hydrogen carbonate solution (80 mL), the organic phase separated, washed with water (80 mL) and saturated brine (80 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give a cream solid. The crude product was purified by chromatography on silica eluting with a solvent gradient of 0 to 20% ethyl acetate in hexanes to give 4-(tert-butyl)-2-(6-(trifluoromethyl)pyridazin-3-yl)phenol (0.282 g, 81% yield) as a cream solid.

Provenance & Evidence