Sulfur Dioxide → HCID 19434080, compound

Participants

Reaction Steps

To a solution of the product from Step D (3.25 g, 12.5 mmol) in anhydrous THF (60 mL) under nitrogen at -70° C. was added n-butyllithium (2.5M, 12.5 mL, 31.4 mmol) over 5 min. The suspension was stirred for 1 h before a stream of sulfur dioxide was passed over the surface of the reaction mixture for 5 min. The mixture was warmed to ambient temperature and evaporated to give a residue which was combined with water (100 mL); this mixture was cooled (ice bath) and hydroxylamine-O-sulfonic acid (4.24 g, 37.5 mmol) and NaOAc (8.5 g, 62.5 mmol) were added. The reaction mixture was stirred at ambient temperature for 18 h and extracted with ethyl acetate (2×200 mL). The combined extracts were dried (MgSO4), filtered, and evaporated to a residue which was purified by column chromatography (silica, 50% ethyl acetate/hexane) to give a viscous oil (4.20 g, 98%).

Provenance & Evidence