反应详情

A mixture of 3,6-diformylindole (1 g), methyl(triphenylphosphoranylidene)acetate (7.76 g) and dry dioxane (50 ml) was stirred and heated under reflux for 6 hr under an atmosphere of nitrogen. The solvent was evaporated, the residue extracted with several portions of ether, the ether extracts evaporated and the crude product purified by flash chromatography, eluting with 2:3 ethyl acetate:hexane, to give dimethyl E,E-indole-3,6-diacrylate (1.2 g, 73%) as a yellow solid; partial NMR (250 MHz, DMSO-d6): 3.71(s, 3H, OCH3), 3.73(s, 3H, OCH3), 6.40(d, J=16.0 Hz, 1H, olefinic H); 6.60(d, J=16.0 Hz, 1H, olefinic H); 12.02(br s, 1H, NH).

1. temperatureheated
2. temperatureunder reflux for 6 hr under an atmosphere of nitrogen
3. customThe solvent was evaporated
4. extractionthe residue extracted with several portions of ether
5. customthe ether extracts evaporated
6. customthe crude product purified by flash chromatography
7. washeluting with 2:3 ethyl acetate