Hexane → (S)-4-benzyl-3-butyryloxazolidin-2-one

Temperature

-78 °C

(S)-4-benzyl-2-oxazolidinone (2.26 g, 15.0 mmol) and 30 ml of dehydrated tetrahydrofuran were mixed, which was cooled to −78° C. under an atmosphere of argon. Under stirring, 1.6 mol/l solution of n-butyl lithium in hexane (10.3 ml, 16.5 mmol) was added dropwise for over 10 minutes and the mixture was stirred for 30 minutes as it was. Next, butyryl chloride (1.56 ml, 15.0 mmol) dissolved into 30 ml of dehydrated tetrahydrofuran was added dropwise for over 10 minutes and the mixture was stirred for 30 minutes, followed by stirring for 3 hours at room temperature. Saturated aqueous solution of ammonium chloride was added to the reaction mixture and concentrated. Water was added to the residue, which was extracted with ethyl acetate. The extract was washed with water and with brine, then dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=1:1 v/v) to obtain 3.64 g (98%) of the title compound as a colorless oil.

1. stirringthe mixture was stirred for 30 minutes as it
2. additionwas added dropwise for over 10 minutes
3. stirringthe mixture was stirred for 30 minutes
4. stirringby stirring for 3 hours at room temperature
5. concentrationconcentrated
6. additionWater was added to the residue, which
7. extractionwas extracted with ethyl acetate
8. washThe extract was washed with water and with brine
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated
11. customThe residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=1:1 v/v)

ORD record

ord-46352f7e80e94cb4959dfe34e5aec7e8

Source dataset

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06506797B1