Triethylamine → HCID 86761235, compound

Participants

Reaction Steps

To a solution of (2R,3R)-1-(tert-butyl-dimethyl-silyloxy)-3-(3,4-dichloro-phenyl)-butan-2-ol (4.63 g, 13.2 mmol) in DCM (44 mL) at 0° C. were added Et3N (4.6 mL, 33.0 mmol), DMAP (81.0 mg, 0.7 mmol), and MsCl (2.2 ml, 28.4 mmol). The mixture was stirred overnight at rt. The reaction was quenched with water (100 mL) and extracted with DCM (3×). The combined organic layers were dried (Na2SO4) and concentrated to yield an orange oil. The product was purified by flash chromatography (Et2O/hexanes) to afford 4.99 g (88%) of the desired product as a colorless liquid. 1H NMR (400 MHz, CDCl3): 7.39 (d, J=8.3, 1H), 7.35 (d, J=2.1, 1H), 7.12 (dd, J=8.3, 2.1, 1H), 4.72-4.69 (m, 1H), 3.71 (dd, J=11.4, 5.7, 1H), 3.64 (dd, J=11.4, 4.3, 1H), 3.24-3.18 (m, 1H), 2.81 (s, 3H), 1.36 (d, J=7.2, 3H), 0.90 (s, 9H), 0.06 (s, 3H), 0.06 (s, 3H).

Provenance & Evidence