tert-Butanol → 1-(Tert-butoxy)-3-(4-(2-(4-(3-chloro-2-hydroxypropoxy)phenyl)propan-2-yl)phenoxy)propan-2-ol

Participants

Reaction Steps

To a solution of racemic 1-chloro-3-(4-(2-(4-(oxiran-2-ylmethoxy)phenyl)propan-2-yl)phenoxy)propan-2-ol (300 mg, 0.8 mmol, 1 equiv) in t-Butanol (5 mL) was added solid Bismuth (III) trifluoromethanesulfonate (10 mg, 0.015 mmol, 1/50 equiv) in one portion and the mixture was stirred at room temperature for 12 h. Sodium bicarbonate was added (0.5 mL), the organic solvent was evaporated under reduced pressure, and the residue was extracted with dichloromethane (3×10 mL). The organic layer was washed with deionized water (2×10 mL), was dried over anhydrous magnesium sulfate, was filtered, and was concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel (eluent: 40% to 80% ethyl acetate in hexane) to provide 1-(tert-butoxy)-3-(4-(2-(4-(3-chloro-2-hydroxypropoxy)phenyl)propan-2-yl)phenoxy)propan-2-ol (100 mg, 28%) as a foam.

Provenance & Evidence