Sulfur Dioxide → HCID 19433999, compound

Participants

Reaction Steps

To a mixture of the product from Step D (3.25 g, 9.85 mmol) in anhydrous THF (40 mL) under nitrogen at -70° C. was added n-butyllithium (2.5M in hexanes, 9.06 mL, 22.7 mmol). The mixture was stirred for 7 min before sulfur dioxide gas was passed over the solution for about 5 min. The resulting mixture was warmed to ambient temperature and evaporated to a residue which was mixed with ice-water (150 mL), hydroxylamine-O-sulfonic acid (3.34 g, 29.6 mmol) and sodium acetate (6.20 g, 45.6 g) and stirred for 4 h at ambient temperature. The reaction mixture was extracted with ethyl acetate (2×100 mL) and the combined extracts were dried over magnesium sulfate and evaporated to a residue which was purified by column chromatography (silica, 5% to 10% methanol/methylene chloride) to give a glass (3.10 g, 77%).

Provenance & Evidence