Reaktion #54586

Reaktionsgleichung

water

potassium-t-butoxide

t-butanol

t-butanol

cis-1,2-bis(bromomethyl)cyclobutane

diethylmalonate

→

3,3-bis(ethoxycarbonyl)bicyclo-[3.2.0]heptane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a 250 ml round-bottomed flask equipped with mechanical stirring
2. 2
   Temperaturreflux
3. 3
   workup.ADDITIONcondenser, addition funnel and argon inlet
4. 4
   TemperaturThe reaction mixture was refluxed
5. 5
   TemperaturThe reaction mixture was refluxed for 15 hr
6. 6
   TemperaturThe reaction mixture was cooled by external application of an ice-water bath
7. 7
   ExtraktionThe mixture was extracted with ether
8. 8
   WaschenThe ether extracts were washed with 3 N hydrochloric acid and 5% aqueous sodium bicarbonate
9. 9
   Trocknendried (MgSO4)
10. 10
    Filtrationfiltered
11. 11
    workup.DISTILLATIONdistilled in vacuo

Vorschrift

In a 250 ml round-bottomed flask equipped with mechanical stirring, reflux condenser, addition funnel and argon inlet was placed 20.2 g of cis-1,2-bis(bromomethyl)cyclobutane, 12.4 ml diethylmalonate, and 72 ml of dry t-butanol. The reaction mixture was refluxed and a solution of 19.9 g of potassium-t-butoxide in 123 ml of t-butanol was added over 6.0 hr. The reaction mixture was refluxed for 15 hr. The reaction mixture was cooled by external application of an ice-water bath and an equal volume of water added. The mixture was extracted with ether. The ether extracts were washed with 3 N hydrochloric acid and 5% aqueous sodium bicarbonate, then dried (MgSO4), filtered and distilled in vacuo to yield 10.3 g of 3,3-bis(ethoxycarbonyl)bicyclo-[3.2.0]heptane as a clear oil, bp 100°-105° C. (vacuum pump).

Quelle