Tetrahydrofuran → N-(1-(2-fluoro-5-nitrophenyl)ethylidene)-2-methylpropane-2-sulfinamide

Participants

Reaction Steps

A 250 ml RBF was charged with 2-methyl-2-propanesulfinamide (3.64 g, 30.0 mmol) and 1-(2-fluoro-5-nitrophenyl)ethanone (5.00 g, 27.3 mmol). THF (55 ml) was added and the resulting slurry was stirred for 5 min until full dissolution was observed. Titanium(IV) ethoxide, technical grade (11.30 ml, 54.6 mmol) was added and the mixture was stirred at 70° C. for 2 h. The mixture was cooled to RT and diluted with 70 ml brine. After stirring for 15 min, EtOAc (50 ml) was added to the mixture and the organic layer was decanted. The aqueous suspension was extracted twice with EtOAc, and the organic fractions were combined, washed with brine and concentrated in vacuo. The residue was purified by FC on 120 g RediSep Gold column using a solvent gradient of 5-50% EtOAc in heptane to afford N-(1-(2-fluoro-5-nitrophenyl)ethylidene)-2-methylpropane-2-sulfinamide (5.88 g, 20.54 mmol, 75% yield) as yellow oil, which crystallized slowly.

Provenance & Evidence