Tetrahydrofuran → (R)-4-(2,4-difluorophenyl)oxazolidin-2-one

To a stirred mixture of (R)-2-amino-2-(2,4-difluorophenyl)ethanol hydrochloride (0.58 g, 2.8 mmol) in THF (18 mL) was added Et3N (1.2 mL, 8.9 mmol). The reaction mixture was cooled in an ice bath under N2. A solution of triphosphene (0.33 g, 1.1 mmol) in THF (10 mL) was added. The reaction was allowed to warm to ambient temperature and stirred for 2 hours. The reaction mixture was partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by column chromatography (EtOAc/hexane, 1:1) to give (R)-4-(2,4-difluorophenyl)oxazolidin-2-one (0.50 g, 91%).

1. temperatureThe reaction mixture was cooled in an ice bath under N2
2. customThe reaction mixture was partitioned between EtOAc and saturated aqueous NaHCO3
3. extractionThe aqueous layer was extracted with EtOAc
4. washThe combined organic layers were washed with brine
5. customdried
6. concentrationconcentrated
7. customThe residue was purified by column chromatography (EtOAc/hexane, 1:1)

ORD record

ord-0c459ff9b9324640ac9062f82abb4cee

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865726B2