Réaction #2006464

Équation de réaction

diethyl diallylmalonate

sodium cyanide

DMSO

→

702

Rendement 78.1%

4-Carbethoxy-1,6-heptadiene

Rendement 78.1%

Solvants

water

Conditions de réaction

Traitement

1. 1
   TempératureAfter being cooled to r.t.
2. 2
   Extractionthe product was extracted into hexane (4×100 mL)
3. 3
   AutreAfter evaporation of the solvent at reduced pressure
4. 4
   workup.DISTILLATIONthe residue was distilled (42-43° C./1 Torr)

Mode opératoire

A mixture of diethyl diallylmalonate (701; 50 g, 208 mmol), sodium cyanide (20.7 g, 422 mmol) and DMSO (166 mL) was heated at 160° C. for 6 h. After being cooled to r.t., the mixture was added to 400 mL of water and the product was extracted into hexane (4×100 mL). After evaporation of the solvent at reduced pressure, the residue was distilled (42-43° C./1 Torr) to give 27.34 g (78%) of 702 as a colorless liquid. 1H NMR (400 MHz, CDCl3) δ 5.80-5.70 (m, 2H, 2 CH═CH2), 5.10-5.02 (m, 4H, 2 CH═CH2), 4.14 (q, 2H, J=7.2 Hz, OCH2), 2.54-2.48 (m, 1H, CH), 2.41-2.34, 2.29-2.23 (2m, 4H, 2CH2), 1.25 (t, J=7.2 Hz, 3H, CH3).

Source