반응 #334877

반응 방정식

sodium

diethyl malonate

5-bromo-1-pentene

diethyl ether

sodium chloride

→

diethyl (4-pentenyl)malonate

수율 58.2%

용매

ethanol

반응 조건

후처리

1. 1
   온도the mixture was heated
2. 2
   온도After cooling the reaction mixture
3. 3
   기타The aqueous phase was separated
4. 4
   추출back-extracted twice with 200 ml of diethyl ether each time
5. 5
   세척The organic phases were washed twice with 150 ml of semi-saturated sodium chloride solution each time
6. 6
   건조dried over sodium sulphate
7. 7
   여과filtered
8. 8
   농축concentrated
9. 9
   기타Chromatographic separation of the resulting, yellow liquid (55.2 g) on silica gel with hexane/ethyl acetate (vol. 95:5)

실험 절차

7.05 g of sodium were dissolved in a solution of 40 g of diethyl malonate in 175 ml of ethanol. The still warm solution (50° C.) was treated dropwise within 15 minutes with 45.6 g of 5-bromo-1-pentene and the mixture was heated to boiling for 2 hours. After cooling the reaction mixture was poured into 500 ml of diethyl ether and 300 ml of semi-saturated sodium chloride solution. The aqueous phase was separated and back-extracted twice with 200 ml of diethyl ether each time. The organic phases were washed twice with 150 ml of semi-saturated sodium chloride solution each time dried over sodium sulphate, filtered and concentrated. Chromatographic separation of the resulting, yellow liquid (55.2 g) on silica gel with hexane/ethyl acetate (vol. 95:5) gave 33.2 g of diethyl (4-pentenyl)malonate as a colourless liquid.

출처