Phosgene → (s)-Tetrahydrofurfurylisocyanate

Participants

Reaction Steps

To a solution of phosgene (2 mL of a ˜20% in toluene, 4.44 mmol) in 5 mL of dichloromethane at 0° C. was added a solution of (S)-tetrahydrofurfurylamine (0.15 mL, 1.48 mmol) and triethylamine (0.45 mL, 3.26 mmol) in 4 mL of dichloromethane dropwise over 20 min. The reaction mixture was stirred for 2.5 h at room temperature. The solvent was removed under reduced pressure, and the resulting residue was dissolved in ether. The triethylamine hydrochloride salt was removed by filtration. Concentration afforded 46A as a clear oil in quantitative yield.

Provenance & Evidence