反应详情

To a solution of 3-methoxypropan-1-ol (15.9 mL, 166 mmol) in CH2Cl2 (75 mL) and pyridine (50 mL) was added 4-(dimethylamino)pyridine (1.0 g, 8.3 mmol) followed by p-toluenesulfonyl chloride (31.7 g, 166 mmol). The mixture was allowed to stir at ambient temperature for 72 hours then was quenched with 5% aqueous HCl (20 mL), extracted with CH2Cl2 (3×10 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 (31 g, 127 mmol, 76% yield). MS (DCI/NH3) m/z 262 (M+NH4)+.

1. customthen was quenched with 5% aqueous HCl (20 mL)
2. extractionextracted with CH2Cl2 (3×10 mL)
3. dry with materialThe combined organic extracts were dried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. customPurification by column chromatography (SiO2, 75% hexanes in EtOAc)