反应详情

To a suspension of 1-cyclohexylmethyl-7-methoxy-1H-indole-3-carboxylic acid (5 g, 17.4 mmol) in dichloromethane (100 ml) was added oxalyl chloride (3.04 ml, 34.8 mmol) and the resulting solution stirred overnight. Excess solvent and reagent were then removed by evaporation. To the resulting residue was added copper (I) cyanide (6.2 g, 69.6 mmol), toluene (200 ml) and acetonitrile (10 ml) and the resulting reaction mixture heated at reflux for 7 hours. A further portion of copper (I) cyanide (1.6 g, 17.9 mmol) was then added and the reaction mixture heated at reflux overnight. The reaction mixture was cooled and filtered through a pad of dicalite. The dicalite was washed with acetonitrile and the combined filtrate evaporated to leave a red solid. The solid was purified by flash column chromatography eluting with 50% (v/v) dichloromethane in heptane to afford (1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)-oxoacetonitrile (4.7 g, 14.7 mmol).

1. customExcess solvent and reagent were then removed by evaporation
2. customthe resulting reaction mixture
3. temperatureheated
4. temperatureat reflux for 7 hours
5. temperaturethe reaction mixture heated
6. temperatureat reflux overnight
7. temperatureThe reaction mixture was cooled
8. filtrationfiltered through a pad of dicalite
9. washThe dicalite was washed with acetonitrile
10. customthe combined filtrate evaporated
11. customto leave a red solid
12. customThe solid was purified by flash column chromatography
13. washeluting with 50% (v/v) dichloromethane in heptane