Water → (R)-1-(6-(Trifluoromethyl)pyridin-3-yl)ethane-1,2-diol

Participants

Reaction Steps

A 100 mL flask was charged with tert-butyl alcohol (49 mL), water (49 mL), and AD-mix-(3 (13.78 g). Stirring at room temperature produced two clear phases. The mixture was cooled to 0° C. and 2-(trifluoromethyl)-5-vinylpyridine (1.7 g, 9.8 mmol) was added at once. The heterogeneous slurry was stirred vigorously at −20° C. overnight. TLC indicated completion of the reaction. While the mixture was stirred at 0° C., solid sodium sulfite (15 g, 0.12 mol) was added and the mixture was allowed to warm to rt and stirred for 1 hour. EtOAc was added to the reaction mixture, and after separation of the layers, the aqueous phase was further extracted with EtOAc. The combined organic layers were dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by silica gel column (MeOH/CH2Cl2: 0-10%) to afford the title compound as a white solid.

Provenance & Evidence