反应详情

温度

0 °C

(R)-1-Pyridin-4-yl-ethanol (0.160 g) was dissolved in THF (10 mL) and cooled to 0° C. nBuLi (2.5 M in hexanes, 0.52 mL) was added slowly and the reaction was stirred at 0° C. for 5 min. Toluenesulfonyl chloride (0.250 g) was added and the stirring was continued for 30 min. NaN3 (0.30 g) was added, the reaction was warmed to RT and stirred overnight. The mixture was added to H2O and the layers were separated. The aqueous layer was extracted with Et2O and the combined organic phases were dried over Na2SO4, filtered and evaporated in vacuo to yield a yellow oil. This crude material was purified by silica gel chromatography (30 g, 33 to 75% Et2O/hexanes w/1% Et3N) to afford (S)-4-(1-azido-ethyl)-pyridine as a clear oil.

1. additionwas added slowly
2. waitthe stirring was continued for 30 min
3. temperaturethe reaction was warmed to RT
4. stirringstirred overnight
5. customthe layers were separated
6. extractionThe aqueous layer was extracted with Et2O
7. dry with materialthe combined organic phases were dried over Na2SO4
8. filtrationfiltered
9. customevaporated in vacuo
10. customto yield a yellow oil
11. customThis crude material was purified by silica gel chromatography (30 g, 33 to 75% Et2O/hexanes w/1% Et3N)