反应详情

温度

0 °C

To a 25 mL round bottom flask is placed (tetrahydro-2H-pyran-4-yl)methanol (350 mg, 3 mmol), followed by dichloromethane (DCM, 15 mL). The solution is cooled to 0° C. and is then treated with methanesulfonyl chloride (0.24 mL, 3.15 mmol) and triethylamine (0.88 mL, 6.3 mmol). The reaction is complete after 30 min. and is then quenched with water and diluted with DCM (10 mL). The layers are then partitioned, and the aqueous layer is extracted with DCM (3×10 mL). The combined organics are dried over Na2SO4, filtered and concentrated. The crude mesylate is then dissolved in DMF (10 mL), to which sodium azide (410 mg, 6.3 mmol) is added and then heated to 75° C. for 4 h. The reaction is then cooled to room temperature, quenched with water (10 mL) and extracted with diethyl ether (3×20 mL). The combined organics are then washed with water (3×10 mL), dried over MgSO4, filtered, and concentrated to give 4-(azidomethyl)-tetrahydro-2H-pyran as a colorless liquid. 1H NMR (CDCl3, 400 MHz) δ 4.01-3.97 (m, 2H), 3.39 (td, J=11.9, 2.1 Hz, 2H), 3.18 (d, J=6.8 Hz, 2H), 1.86-1.75 (m, 1H), 1.67-1.64 (m, 2H), 1.40-1.29 (m, 2H).

1. customTo a 25 mL round bottom flask is placed
2. customis then quenched with water
3. additiondiluted with DCM (10 mL)
4. customThe layers are then partitioned
5. extractionthe aqueous layer is extracted with DCM (3×10 mL)
6. dry with materialThe combined organics are dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. additionis added
10. temperatureheated to 75° C. for 4 h
11. temperatureThe reaction is then cooled to room temperature
12. customquenched with water (10 mL)
13. extractionextracted with diethyl ether (3×20 mL)
14. washThe combined organics are then washed with water (3×10 mL)
15. dry with materialdried over MgSO4
16. filtrationfiltered
17. concentrationconcentrated