2-(Chloroethoxy)ethanol → 2-(2-Azidoethoxy)ethan-1-ol

A solution of 2-(2-chloro-ethoxy)-ethanol (15 g, 0.12 mol) and sodium azide (15.7 g, 2 equiv.) in H2O (50 ml) was heated at 90° C. for 16 h. The reaction mixture was cooled down to RT then extracted with CH2Cl2 (6×50 ml). The combined organic layers were dried over MgSO4 and filtrated. The solvents were removed under reduced pressure to give azide 2 as a colorless liquid (15 g, 95%). 1H and 13C NMR spectra matched the literature data (Cheng, H. et al. J. Med. Chem. 2005, 48, 645-653).

1. extractionthen extracted with CH2Cl2 (6×50 ml)
2. dry with materialThe combined organic layers were dried over MgSO4
3. filtrationfiltrated
4. customThe solvents were removed under reduced pressure

ORD record

ord-bb483a33c7a24b8ea90126da72e4e756

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073969B2