Sodium Chloride → 2-Methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide

3-Oxetanone (3 g, 41.63 mmol), tert-butyl sulfinamide (5.55 g, 45.8 mmol) and titanium (IV) ethoxide (13.5 mL, 62.4 mmol) were stirred in THF (200 mL) at 40° C. for 72 hours. The mixture was cooled to room temperature and poured into a rapidly stirred aqueous solution of saturated sodium chloride (200 mL). The resulting suspension was filtered through Celite© and the filter cake washed with ethyl acetate. The organic layer was separated and washed with brine, then dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford the title compound as an oil (1.37 g, 19% yield).

1. filtrationThe resulting suspension was filtered through Celite©
2. washthe filter cake washed with ethyl acetate
3. customThe organic layer was separated
4. washwashed with brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated in vacuo
7. customThe residue was purified by silica gel column chromatography

ORD record

ord-17f39cb607d442d198d5e5c92bc6ec77

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09079878B2