Diethyl Ether → HCID 11171039, compound

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).

1. stirringstirred for a few minutes
2. customThe organic layer was separated from the aqueous layer
3. extractionthe aqueous phase was extracted three times with ether-dichloromethane mixture
4. washThe combined organic extracts were washed with saturated aqueous solution of sodium chloride
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated on rotory evaporator
7. customto give an oil

ORD record

ord-196b8739cc3c4d52bcfd900e2da40afc

Source dataset

uspto-grants-1993_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05254682