Hexane → HCID 10491506, compound

Temperature

-78 °C

To a solution (0.49 M) of (4S)-4-benzyl 1,3-oxazolidinone in THF cooled to −78° C. was added dropwise n-BuLi in hexane (2.5 M, 1.1 eq). The resulting solution was stirred at −78° C. for 30 min, then a solution of 4-pentenoyl chloride in THF (4 M, 1.1 eq) was added dropwise. The resulting mixture was stirred at −78° C. for 20 min and then allowed to reach 0° C., where it was stirred for another 40 min. The reaction was quenched by addition of sat. aq. NH4Cl before partitioning between H2O and EtOAc. The layers were separated and the aqueous phase re-extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by FC eluting with PE/EtOAc (10:1) to give the product as a colourless oil (72%). (ES+) m/z 260 (M+H)+.

1. stirringThe resulting mixture was stirred at −78° C. for 20 min
2. customto reach 0° C.
3. stirringwhere it was stirred for another 40 min
4. customThe reaction was quenched by addition of sat. aq. NH4Cl
5. custombefore partitioning between H2O and EtOAc
6. customThe layers were separated
7. extractionthe aqueous phase re-extracted with EtOAc
8. washThe combined organic extracts were washed with brine
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customThe residue was purified by FC
13. washeluting with PE/EtOAc (10:1)

ORD record

ord-cff3dffd2f8d4fb4a6db22762298f5da

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989438B2