Ethylene Oxide → HCID 90066757, compound

Temperature

-78 °C

Into a 250-mL three neck round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of N,N,2-trimethyl-1H-imidazole-1-sulfonamide (compound 282.1, 6.4 g, 33.8 mmol) in tetrahydrofuran (50 mL). This was followed by the addition of n-BuLi (2.5M in hexane) (16.3 mL, 40.6 mmol) dropwise with stirring at −78° C. The reaction mixture was stirred for 1 h at −78° C. Oxirane (12.1 mL, 242.89 mmol) was added dropwise at −30° C. The reaction mixture was stirred for 2 h at room temperature, then quenched with 10 mL of water. The aqueous phase was extracted with 3×30 mL of ethyl acetate. The combined organic layers were washed with 3×20 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography with EtOAc:MeOH (40:1) as the eluent to yield 3.4 g (43%) of the title compound as a white solid.

1. customInto a 250-mL three neck round-bottom flask, which was purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. stirringThe reaction mixture was stirred for 1 h at −78° C
4. stirringThe reaction mixture was stirred for 2 h at room temperature
5. customquenched with 10 mL of water
6. extractionThe aqueous phase was extracted with 3×30 mL of ethyl acetate
7. washThe combined organic layers were washed with 3×20 mL of brine
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by silica gel chromatography with EtOAc:MeOH (40:1) as the eluent

ORD record

ord-a9390ba08f1c4806ad603beef5113c23

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2