反应详情

To a solution of 2-(tetrahydropyran-4-yl)-ethanol (1.5 g, 11.5 mmol) in 10 mL of CH2Cl2 and 7 mL of pyridine was added p-toluenesulfonyl chloride (2.4 g, 12.7 mmol) portion wise over 15 minutes. The mixture stirred at ambient temperature for 3 hours and was quenched with 10 mL of saturated, aqueous NaHCO3. The layers were separated and the aqueous layer was extracted with three 5 mL of portions of CH2Cl2. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification via column chromatography (SiO2, 70% hexanes in ethyl acetate) afforded the title compound. MS (DCI/NH3) m/z 302 (M+NH4)+.

1. customwas quenched with 10 mL of saturated, aqueous NaHCO3
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with three 5 mL of portions of CH2Cl2
4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customPurification via column chromatography (SiO2, 70% hexanes in ethyl acetate)