Propargyl alcohol → (5R)-3-(3-Fluoro-4-iodophenyl)-5-[(4-hydroxymethyl-1H-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one

Participants

Reaction Steps

A mixture of (5R)-3-(3-fluoro-4-iodophenyl)-5-azidomethyl-1,3-oxazolidin-2-one (10 g, 28 mmol) and propargyl alcohol (3.2 mL, 56 mmol) in acetonitrile (80 mL) was treated with CuI (526 mg, 2.8 mmol) and then stirred overnight. The solidified reaction mixture was extracted with ethyl acetate:acetonitrile, washed with water, and dried over magnesium sulfate, and then evaporated under reduced pressure to give a crude product sufficiently pure for further use (12.3 g, quantitative).

Provenance & Evidence