反应详情

To a solution of 3,3,3-trifluoropropan-1-ol (5.0 g, 43.8 mmol) in CH2Cl2 (25 mL) and pyridine (25 mL) was added 4-(dimethylamino)pyridine (0.27 g, 2.2 mmol) followed by p-toluenesulfonyl chloride (8.4 g, 43.8 mmol). The mixture was allowed to stir at ambient temperature for 72 h then was quenched with 5% aqueous HCl (20 mL). The layers were separated and the aqueous phase was extracted with CH2Cl2 (3×7 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by column chromatography (SiO2, 75% hexanes in EtOAc) afforded the title compound (8.0 g, 29.8 mmol, 68% yield). MS (DCI/NH3) m/z 286 (M+NH4)+.

1. customthen was quenched with 5% aqueous HCl (20 mL)
2. customThe layers were separated
3. extractionthe aqueous phase was extracted with CH2Cl2 (3×7 mL)
4. dry with materialThe combined organic extracts were dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customPurification by column chromatography (SiO2, 75% hexanes in EtOAc)