Sodium hydride → HCID 54712966, compound

Participants

Reaction Steps

A solution of 4-hydroxy-2(5H)-furanone (1.47 g, 14.7 mmol) in tetrahydrofuran (30 ml) was slowly added at 0° C. to a suspension of sodium hydride (80% oil dispersion) (530 mg, 14.7 mmol) in tetrahydrofuran (30 ml). The mixture was stirred at room temperature for 15 minutes, then a solution of 4-trifluoromethylphenyl isocyanate (2.75 g, 14.7 mmol) in tetrahydrofuran (20 ml) was added and the mixture stirred overnight at room temperature. At the end of the reaction, the insoluble product was filtered off and the solvent removed under reduced pressure. Crude product was suspended in water (60 ml) and methanol (6 ml) and the mixture acidified to pH 2 with concentrated HCl; the solid thus obtained was filtered and crystallised from acetone giving 1.75 g (41%) of pure N-(4-trifluoromethylphenyl)-4-hydroxy-2-oxo-(5H)-furan-3-carboxamide as a white solid. m.p.204-206° C. (dec.)

Provenance & Evidence