Sodium Dithionite → HCID 86744500, compound

The quaternary salt prepared in Example 94 (780 mg, 1.5 mmol) was dissolved in degassed, deionized water (200 mL) and acetonitrile (10 mL). Sodium dithionite (780 mg, 4.5 mmol) and sodium bicarbonate (630 mg, 7.5 mmol) were combined and added to the solution at room temperature. The reaction was continued for 1 hour, while nitrogen gas was slowly bubbled through the solution. The partially precipitated product was extracted repeatedly with ether (8×30 mL). The extracts were combined, washed with water (25 mL) and dried over magnesium sulfate. The drying agent was filtered and the solvent was removed from the filtrate under reduced pressure. The oily residue was dissolved in methylene chloride (3×5 mL) and removed under reduced pressure. The resulting foam was rinsed with anhydrous ether (3 mL) and the solvent was removed under vacuum. The final product weighed 390 mg, giving a 66% yield. The hygroscopic solid foam was stored under nitrogen at -100° C. It had the structural formula: ##STR127## as confirmed by UV, NMR and elemental analyses.

1. customin degassed
2. additionadded to the solution at room temperature
3. customwas slowly bubbled through the solution
4. extractionThe partially precipitated product was extracted repeatedly with ether (8×30 mL)
5. washwashed with water (25 mL)
6. dry with materialdried over magnesium sulfate
7. filtrationThe drying agent was filtered
8. customthe solvent was removed from the filtrate under reduced pressure
9. dissolutionThe oily residue was dissolved in methylene chloride (3×5 mL)
10. customremoved under reduced pressure
11. washThe resulting foam was rinsed with anhydrous ether (3 mL)
12. customthe solvent was removed under vacuum
13. customgiving a 66% yield
14. customwas stored under nitrogen at -100° C

ORD record

ord-f6d227c5599040509ee176389be2c314

Source dataset

uspto-grants-1991_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05002935