Ethyl ketone → HCID 22350059, compound

Temperature

-10 °C

To a solution of ethyl vinylether (10 mL, 104 mmol) in THF (50 mL) at −78° C. was added tert-BuLi (1.7M, pentane, 45 mL, 76 mmol) dropwise. The mixture was stirred at −10° C. for 15 min then cooled to −78° C. and 3-pentanone (5.0 g, 58 mmol, in 5 mL of THF) was added dropwise. The resulting reaction mixture was allowed to warm slowly to 21° C., then diluted with a saturated ammonium chloride solution and ethyl acetate. The organic extract was stirred with 6 mL of HCl 2% for 18 h then washed (H2O, brine), dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (eluting with hexane/ethyl acetate, 95:5) to provide the 3-ethyl-3-hydroxy-pentan-2-one compound as an oil.

1. temperaturethen cooled to −78° C.
2. customThe resulting reaction mixture
3. temperatureto warm slowly to 21° C.
4. extractionThe organic extract
5. stirringwas stirred with 6 mL of HCl 2% for 18 h
6. washthen washed (H2O, brine)
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customThe residue was purified by flash chromatography (eluting with hexane/ethyl acetate, 95:5)

ORD record

ord-8df8a3647c484f829235ac37ae7210fe

Source dataset

uspto-grants-2005_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06919353B2