hydroxylamine-O-sulfonic acid → HCID 9906472, compound

Participants

Reaction Steps

Tetrabutylammonium fluoride (0.83 mL, 0.83 mmol, 1M in THF) was added to the silane from Step 1 (0.121 g, 0.277 mmol) and dry THF (0.5 mL). The resulting mixture was refluxed for 1 hour then cooled to room temperature. To the reaction mixture was added sequentially NaOAc (0.103 g, 1.26 mmol), water (1.5 mL), and H2NOSO3H (0.157 g, 1.38 mmol) and the reaction was stirred for 1 hour at room temperature. The reaction mixture was diluted with ethyl acetate (5.0 mL) and water (5.0 mL). The layers were separated, and the organic layer was washed with saturated NaHCO3 (5.0 mL), water (5.0 mL), and brine (5.0 mL) then dried over MgSO4. The solution was filtered, the solids washed with ethyl acetate, and the solvents removed under reduced pressure. The crude product was purified by silica gel chromatography to afford 0.087 g (97%) of product as a white solid.

Provenance & Evidence