Hydrogen Peroxide → HCID 53730440, compound

Participants

Reaction Steps

A solution of the oxazolidinone (2) (0.57 g, 1.23 mmol) in THF/water (4:1, 25 ml) was cooled in an ice bath and treated with hydrogen peroxide solution (27.5 wt. %, 4.9 mmol, 0.56 ml, 4 eq). The mixture was stirred for a few min. then treated dropwise with a solution of lithium hydroxide monohydrate (1.23 mmol, 52 mg, 1.0 eq) in water (5 ml). The reaction was stirred for 1.5 hr then treated with a 10% aqueous solution of sodium sulphite (5 ml). The reaction mixture was adjusted to pH 12-13 with 1M NaOH and then partitioned between dichloromethane and water. The aqueous layer was separated and acidified with 10% HCl. The aqueous layer was extracted three times with EtOAc. The combined organic layer was washed once with brine, once with NaHCO3 solution, dried (MgSO4) and the solvent removed to give the title compound (3) (0.18 g) as a yellowish oil which was used without further purification. δH (CDCl3) 1.43 (9H, s), 1.51-1.79 (4H, m), 2.32 (3H, s), 2.37 (1H, dd), 2.92 (1H, m), and 7.03-7.12 (4H, m).

Provenance & Evidence