Dimethyl Sulfoxide → (1S)-2-azido-1-(3-chlorophenyl)ethan-1-ol

Participants

Reaction Conditions

Reaction Steps

A mixture of toluene-4-sulfonic acid (S)-2-(3-chlorophenyl)-2-hydroxyethyl ester (16.34 g, 0.050 mol), sodium azide (6.50 g, 0.10 mol) and DMSO (50 ml) was stirred for 2 h at 80° C. Water (100 ml) was added, extracted with hexane-ether (1:1) mixture (2×150 ml). Combined extract was dried over Na2SO4, evaporated. The residue was separated on SiO2 (100 g), hexane-EtOAc, 0 to 20%. Colorless oil, 7.0 g, (0.035 mol, 71%). 1H NMR (300 MHz, DMSO) δ 7.46 (s, 1H), 7.36 (m, 3H), 5.95 (d, J=4.5 Hz, 1H), 4.82 (q, J=5.3 Hz, 1H), 3.35 (m, 2H).

Provenance & Evidence