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

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.

1. customproduced two clear phases
2. temperatureThe mixture was cooled to 0° C.
3. stirringThe heterogeneous slurry was stirred vigorously at −20° C. overnight
4. customcompletion of the reaction
5. stirringWhile the mixture was stirred at 0° C.
6. temperatureto warm to rt
7. stirringstirred for 1 hour
8. customafter separation of the layers
9. extractionthe aqueous phase was further extracted with EtOAc
10. dry with materialThe combined organic layers were dried over anhydrous MgSO4
11. concentrationconcentrated in vacuo
12. customThe residue was purified by silica gel column (MeOH/CH2Cl2: 0-10%)

ORD record

ord-79b1c1e90a2f46b89443b13d26c57fe8

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946439B2