Ethyl Acetate → HCID 62469629, compound

Participants

Reaction Steps

To a solution of the above (2-chloro-pyridin-3-yl)-methanol (2.2 g, 15.1 mmol) and DPPA (3.9 mL, 18.2 mmol) in toluene (30 mL) was added DBU (2.9 mL, 18.2 mmol) at room temperature and stirred for 3 h. The reaction was diluted with 3M HCl (30 mL) and Et2O (75 mL). The layers were separated and the aqueous layer was extracted with Et2O (75 mL). The combined organic layers were washed with water (50 mL), brine and dried over MgSO4. The solution was filtered and concentrated in vacuo to yield a yellow oil. Silica gel column chromatography using 95:5 hexanes:EtOAc afforded 2.0 g (77%) of 3-azidomethyl-2-chloro-pyridine as a colorless oil.

Provenance & Evidence