Dimethyl Sulfoxide → Diallylacetic Acid Ethyl Ester

반응식

[CH2:1]([C:4]([CH2:15][CH:16]=[CH2:17])(C(OCC)=O)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:2]=[CH2:3].[C-]#N.[Na+].CS(C)=O>O>[C:5]([CH:4]([CH2:1][CH:2]=[CH2:3])[CH2:15][CH:16]=[CH2:17])([O:7][CH2:8][CH3:9])=[O:6]

참가 물질

반응 조건

온도: 160 °C

실험 절차

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).