Ethylene Oxide → HCID 90030091, compound

Temperature

-78 °C

Into a 50-mL three-neck round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of N,N,4-trimethyl-1H-pyrazole-1-sulfonamide (compound 305.1, 1.19 g, 6.26 mmol) in THF (24 mL) n-BuLi (3 mL, 7.5 mmol, 2.5 M in hexanes) was added to the reaction dropwise at −78° C. The resulting mixture was stirred for 30 min at −78° C. This was followed by the addition of a solution of oxirane (5.6 mL, 113.51 mmol) in THF (4 mL) at −78° C. The reaction mixture was then brought to room temperature and stirred for 3 h. The reaction was quenched with 10 mL of NH4Cl (sat.) and the aqueous phase was extracted with 3×50 mL of EtOAc. The combined organic layers were dried over Na2SO4. The solvent was removed to give the crude product which was purified by silica gel chromatography with hexanes/EtOAc (3:1) as the eluent to furnish 636 mg (44%) of the title compound as light yellow oil.

1. customInto a 50-mL three-neck round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. additionwas added to the reaction dropwise at −78° C
4. customwas then brought to room temperature
5. stirringstirred for 3 h
6. customThe reaction was quenched with 10 mL of NH4Cl (sat.)
7. extractionthe aqueous phase was extracted with 3×50 mL of EtOAc
8. dry with materialThe combined organic layers were dried over Na2SO4
9. customThe solvent was removed
10. customto give the crude product which
11. customwas purified by silica gel chromatography with hexanes/EtOAc (3:1) as the eluent

ORD record

ord-8c119bfd6f7a4d78acd041f9d4ba8f0b

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2