Diethyl Ether → HCID 11171039, compound

Participants

Reaction Steps

To a solution of 2,3-epoxyhexane 33 (4.155 g, 41.48 mmol) in N,N-dimethylformamide (DMF) was added lithium azide (3.8 g, 77.6 mmol) and the resulting mixture was stirred for 48 hours. The reaction mixture was poured into a solvent mixture of ether, dichloromethane and water, and stirred for a few minutes. The organic layer was separated from the aqueous layer and then the aqueous phase was extracted three times with ether-dichloromethane mixture. The combined organic extracts were washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated on rotory evaporator to give an oil. Flash column chromatography of the oil using 10% ethyl acetate in hexane as eluent afforded 34 (5.9 g, 99.3%): 1H NMR (300 MHz, CDCl3) δ3.775 (m, 1H, CHOH), 3.38 (dd, 1H, CHN3), 3.25 (dd, 1H, CHN3), 2.2 (d, 1H, OH), 1.6-1.2 (m, 6H, CH2 's), 0.95 (t, 3H, CH3).

Provenance & Evidence