Diethyl Carbonate → HCID 54216092, compound

Participants

Reaction Steps

A solution of 1.40 g (5.6 mmol) of (S)-3-(4-cyclohexyl-phenylamino)-propane-1,2-diol in 50 ml of toluene was treated with 0.73 g (6.2 mmol) of diethyl carbonate and 0.5 ml of a 1 molar sodium methylate solution and stirred overnight at an oil bath temperature of 110°. After distilling off the solvent the residue was treated with water and 5 ml of 1N hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with sodium chloride solution, dried over magnesium sulfate and the solvent was distilled off. 1.35 g of (S)-3-(4-cyclohexylphenyl)-5-hydroxymethyl-oxazolidin-2-one were obtained in the form of colorless crystals from ethyl acetate/hexane. M.p.: 166°-168°. [α]D =+51.25° (c=0.8/CH3OH).

Provenance & Evidence