Ethylene Oxide → HCID 10512306, compound

Temperature

-78 °C

In a 25 ml flask were placed 11-2 (0.500 g, 3.16 mmol), and anhydrous THF (6 mL). The reaction was flushed with N2 gas and cooled to −78° C. Ethylene oxide (27.3 g, 31 mL, 31.6 mmol) was added dropwise via syringe. Upon completion of addition, the reaction mixture was warmed to room temperature and stirred for 18 hours. The reaction mixture was then quenched with sat. aq. NH4Cl (100 mL) and extracted with EtOAc (2×150 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel flash column chromatography (24 g cartridge), eluting with 0-100% EtOAc/hexanes to give 200 mg (31%) of 11-3. LC/MS: m/z (M+H)=203.2.

1. customIn a 25 ml flask were placed
2. customThe reaction was flushed with N2 gas
3. additionUpon completion of addition
4. temperaturethe reaction mixture was warmed to room temperature
5. customThe reaction mixture was then quenched with sat. aq. NH4Cl (100 mL)
6. extractionextracted with EtOAc (2×150 mL)
7. washThe combined organic layers were washed with brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe crude product was purified by silica gel flash column chromatography (24 g cartridge)
12. washeluting with 0-100% EtOAc/hexanes

ORD record

ord-8cc917f989174daa9088f8f7941a746f

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266881B2