Reaktion #551827

Reaktionsgleichung

sodium bisulfite

magnesium silicate

N-methylmorpholine N-oxide

2-thiabicyclo[2.2.2]oct-5-en-3-one O-[(methylamino)carbonyl]oxime

acetone

→

viscous oil

5,6-Dihydroxy-2-thiabicyclo[2.2.2]octan-3-one O-[(methylamino)carbonyl]oxime

Lösungsmittel

water

tert-butanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter being stirred for 30 minutes
2. 2
   Filtrationthe mixture was filtered
3. 3
   ExtraktionThe filtrate was extracted with ethyl acetate
4. 4
   SonstigeEvaporation of the dried organic solution

Vorschrift

To a solution of 6.5 g (0.048 m) of N-methylmorpholine N-oxide and 5.0 g (0.024 m) of 2-thiabicyclo[2.2.2]oct-5-en-3-one O-[(methylamino)carbonyl]oxime in 20 ml of acetone was added 15 ml of a 0.5% solution of osmium tetroxide in tert-butanol. The reaction mixture was stirred at room temperature for 48 hours, then treated with a slurry of 1 g sodium bisulfite, 15 g of magnesium silicate, and 50 ml of water. After being stirred for 30 minutes, the mixture was filtered. The filtrate was extracted with ethyl acetate, then with methylene chloride. Evaporation of the dried organic solution gave 4.8 g of viscous oil. Purification by dry column chromatography yielded 3.5 g of the title compound as a white solid, m. 123°-5° C.

Quelle