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

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Reaction Steps

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).

Provenance & Evidence