Reaktion #172383

Reaktionsgleichung

hydrogen peroxide

9-borabicyclo[3.3.1]nonane

compound

1-(2-Methyl-4-nitrophenyl)-3-vinylpyridin-2(1H)-one

sodium hydroxide

sodium disulphite

→

3-(2-Hydroxyethyl)-1-(2-methyl-4-nitrophenyl)pyridin-2(1H)-one

Lösungsmittel

tetrahydrofuran

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturWith ice-cooling
2. 2
   Sonstigedoes not exceed 30° C
3. 3
   workup.ADDITIONAfter the addition
4. 4
   Sonstigethe cooling is removed
5. 5
   workup.STIRRINGstirring
6. 6
   ExtraktionThe mixture is repeatedly extracted with ethyl acetate
7. 7
   Sonstigethe organic phase is separated off
8. 8
   Extraktionthe aqueous phase is again extracted with ethyl acetate
9. 9
   WaschenThe combined organic phases are washed with saturated sodium chloride solution
10. 10
    Trocknendried over magnesium sulphate
11. 11
    Sonstigeevaporated to dryness under reduced pressure
12. 12
    Sonstigechromatographed
13. 13
    Einengenconcentrated to dryness under reduced pressure

Vorschrift

With ice-cooling, a solution of 40 g (326 mmol) of 9-borabicyclo[3.3.1]nonane in 650 ml of tetrahydrofuran is added over a period of 45 min to 38 g (148 mmol) of the compound from Example 13A. The mixture is stirred at this temperature for another hour, and a solution of 30 g (747 mmol) of sodium hydroxide in 740 ml of water is then added over a period of 15 min. 151 ml of a 30% strength hydrogen peroxide solution are added such that the temperature does not exceed 30° C. After the addition has ended, the cooling is removed and stirring is continued for a further 30 min. The mixture is repeatedly extracted with ethyl acetate, the combined organic phases are washed with a solution of 780 g (1.63 mol) of sodium disulphite, the organic phase is separated off and the aqueous phase is again extracted with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulphate and evaporated to dryness under reduced pressure. The residue is applied to silica gel and chromatographed using a gradient of cyclohexane and ethyl acetate. The product-containing fractions are combined and concentrated to dryness under reduced pressure. This gives 38 mg (93% of theory) of the desired product.

Quelle