Tetrahydrofuran → HCID 10922077, compound

To a solution of oxazolidin-2-one (4.00 g; 45.9 mmol) in dry tetrahydrofuran (70 ml), a solution of n-butyl lithium in hexane (1.60 N; 30 ml) was added at 0° C., and then 1-bromopropionyl bromide (5.83 ml, 45.9 mmol) was added at the same temperature. After 1 hour, an aqueous solution of saturated potassium dihydrogen phosphate (5 ml) was added to decompose the excess reaction agent. The aqueous layer was extracted with ethyl acetate, and the combined organic layer was washed with brine and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (n-hexane:dichloromethane=1:1) to give 3-(2'-bromopropionyl)oxazolidin-2-one (8.68 g, yield, 84%) as a colorless solid. The sample for analysis was obtained by recrystallization from diethyl ether. M.P., 41° C.

1. extractionThe aqueous layer was extracted with ethyl acetate
2. washthe combined organic layer was washed with brine
3. dry with materialdried over anhydrous magnesium sulfate
4. distillationAfter distilling off the solvent
5. customthe residue was purified by silica gel column chromatography (n-hexane:dichloromethane=1:1)

ORD record

ord-94486c791eb442e0b3c79ead3ae6a54d

Source dataset

uspto-grants-1993_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05231179