Imidazole → HCID 68771119, compound

Participants

Reaction Steps

To a stirred solution of (2R,3R)-3-(3,4-dichloro-phenyl)-butane-1,2-diol (3.20 g, 13.6 mmol) and imidazole (1.39 g, 20.4 mmol) in DCM (28 mL) at rt was added tert-butyldimethylsilyl chloride (TBSCl; 2.15 g, 14.3 mmol). The solution was stirred for 1 h then quenched by addition of satd. aq. NH4Cl (100 mL). The mixture was stirred for 5 min, the layers were separated, and the aqueous layer was extracted with DCM (3×). The combined organic layers were dried (Na2SO4) and concentrated to yield a viscous yellow liquid. The product was purified by flash chromatography (EtOAc/hexanes) to afford 4.52 g (95%) of the desired product as a colorless viscous liquid. 1H NMR (400 MHz, CDCl3): 7.37 (d, J=8.3, 1H), 7.36 (d, J=2.1, 1H), 7.10 (dd, J=8.2, 2.1, 1H), 3.75-3.68 (m, 1H), 3.65 (dd, J=9.9, 3.8, 1H), 3.45 (dd, J=9.9, 7.1, 1H), 2.81 (quint, J=7.0, 1H), 2.37 (d, J=4.0, 1H), 1.25 (d, J=7.2, 3H), 0.89 (s, 9H), 0.07 (s, 3H), 0.06 (s, 3H).

Provenance & Evidence