(Diethylamino)sulfur trifluoride → HCID 15690213, compound

Participants

Reaction Steps

To a stirring solution of 3-azido-2-hydroxypropanal diethyl acetal (7.32 g, 38.73 mmol) in dry benzene (50 mL) was added diethylaminosulfurtrifluoride (DAST; 20.6 mL) at -78° C. After the addition, the solution was stirred at room temperature for an hour, then heated to 70° C. for 12 hours. The reaction was quenched by the addition of methanol at zero degrees C and dilution with water. After dichloromethane extraction, the organic layer was dried over MgSO4 and concentrated in vacuo. The crude product was purified with silica gel column chromatography (hexane:ether=9:1, volume/volume) to yield 3-azido-2-fluoropropanal diethyl acetal as an oil (65 percent); Rf =0.84 EtOAc:hexane=2:3); 1H-NMR (CD3Cl) δ1.215~1.219 (6H, m) 3.526 (2H, dm, J=15.3 Hz), 3.642~3.670 (2H, m), 3.680~3.808 (2H, m), 4.514 (1H, dm, J=45.9 Hz) ppm.

Provenance & Evidence