(Diethylamino)sulfur trifluoride → HCID 178494571, compound

Participants

Reaction Steps

0.5 g of (RS)3-[4-(trans-4-hydroxy-cyclohexyl)-phenyl]-5-methoxymethyl-oxazolidin-2-one was dissolved in 10 ml of methylene chloride and treated at room temperature within 30 minutes with a mixture of 2.2 ml of diethylamino-sulfur trifluoride and 5 ml of methylene chloride. After stirring at room temperature for 2 hours the mixture was poured into 50 ml of ice-water and extracted twice with methylene chloride. The organic phase was washed with sodium chloride solution, sodium hydrogen carbonate solution and again with a sodium chloride solution, dried with magnesium sulfate and concentrated. The residue, 0.6 g of yellow honey, was chromatographed on a 30-fold amount of silica gel with methylene chloride-ethyl acetate (19:1) and yielded 80 mg of (RS)-3-[4-(cis-4-fluoro-cyclohexyl)-phenyl]-5-methoxymethyl-oxazolidin-2-one as a colorless oil. 1H-NMR (CDCl3)ppm: 7.47 (d,2H), 7.24 (d,2H), 4.88 (bd,1H), 4.74 (m,1H), 4.04 (t, 1H), 3.91 (m,1H), 3.64 (d,2H), 3.43 (s,3H), 2.53 (m,1H), 2.16 (m,2H), 1.72 (m,6H).

Provenance & Evidence