Ammonium Chloride → (S)-3-(2-(4-Fluoro-3-methylphenoxy)acetyl)-4-isopropyloxazolidin-2-one

Temperature

-70 °C

To the solution of (S)-( )-4-Isopropyl-2-oxazolidinone (992 mg, 5.6 mmol) in anhydrous 30 mL THF at −70° C. was slowly added n-BuLi (3.5 mL, 5.6 mmol, 1.6 M in hexane) over 15 minutes. The reaction mixture was stirred for 30 min at −70° C. and to it was slowly added a solution of 2-(4-fluoro-3-methylphenoxy)acetyl chloride crude solution in 4 mL THF. The resulting mixture was stirred at −70° C. for 2 h and the temperature was slowly raised over a period of 1 h. The mixture was poured into 30 mL saturated NH4Cl and extracted with ethyl acetate (3×40 mL). The combined organic layers were washed with brine (2×30 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the product isolated by Flash column chromatography eluting with 0% to 50% ethyl acetate/hexane to give 2.2 g of the title compound as a light yellow oil.

1. customat −70° C.
2. customover 15 minutes
3. stirringThe resulting mixture was stirred at −70° C. for 2 h
4. temperaturethe temperature was slowly raised over a period of 1 h
5. extractionextracted with ethyl acetate (3×40 mL)
6. washThe combined organic layers were washed with brine (2×30 mL)
7. dry with materialdried over Na2SO4
8. customThe solvent was removed under reduced pressure
9. customthe product isolated by Flash column chromatography
10. washeluting with 0% to 50% ethyl acetate/hexane

ORD record

ord-6b6ae7314e0244298e77f214b3caf32b

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07879911B2