Reaktion #55583

Reaktionsgleichung

sodiodiethylethylmalonate

xylene

Sodium

diethyl ethylmalonate

water

→

title compound

Diethyl-2-ethyl-2-(3-cyclohexylpropyl)-malonate

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturby heating
2. 2
   TemperaturThe mixture was cooled
3. 3
   Sonstigethe xylene was removed with a filter stick
4. 4
   workup.ADDITIONDry toluene (300 ml distilled from calcium hydride) was added
5. 5
   TemperaturThe mixture was cooled
6. 6
   SonstigeThe phases were separated
7. 7
   Extraktionthe aqueous phase was extracted with 500 ml (2×250 ml) of ether
8. 8
   ExtraktionThe ether extract
9. 9
   Waschenwas washed with 250 ml of saturated sodium chloride solution
10. 10
    Trocknendried over a anhydrous magnesium sulfate
11. 11
    Filtrationfiltered
12. 12
    SonstigeThe solvents were removed in vacuo
13. 13
    workup.DISTILLATIONThe product was distilled at reduced pressure

Vorschrift

Sodium metal (3.16 g, 0.137 g/atom) was dispersed by heating with rapid stirring in 80 ml of dry xylene at 110° to 120° C. The mixture was cooled and the xylene was removed with a filter stick. Dry toluene (300 ml distilled from calcium hydride) was added thereto and followed by the addition of 28.17 g (0.149 mole) of diethyl ethylmalonate. This mixture was slowly heated to 150° C. 3-Cyclohexylpropyl-1-tosylate (28.3 g, 1.1956 mole; prepared by Example 10A) was dissolved in 80 ml of dry toluene. This solution was then added to the sodiodiethylethylmalonate above and the mixture was stirred at 150° C. for 10 hr. The mixture was cooled and poured into 500 ml of water. The phases were separated and the aqueous phase was extracted with 500 ml (2×250 ml) of ether. The ether extract was washed with 250 ml of saturated sodium chloride solution, dried over a anhydrous magnesium sulfate and filtered. The solvents were removed in vacuo. The product was distilled at reduced pressure to yield 19.4 g of the title compound having the following physical characteristics:

Quelle