Chloroform → HCID 136026279, compound

Participants

Reaction Steps

A mixture of diethyl oxalate (4.4 ml) and the product of step (a) (1.1 g; 3.98 mmole) in ethanol (50 ml) was added slowly to freshly prepared sodium ethoxide (0.68 g; 9.99 mmole) in ethanol (80 ml) to give instantly a yellow suspension. After the addition, the mixture was heated to reflux on the steambath for half an hour to give a brown suspension. The mixture was cooled and neutralised with dilute hydrochloric acid to give a bright orange precipitate. This was extraced into chloroform, dried and evaporated to give a bright orange solide. The solid was redissolved in ethanolic hydrogen chloride. The solution was heated to reflux on a steambath for 3 hours. The mixture was cooled and was treated with water. After concentration, this was extracted into chloroform. The organic extract was washed with water, dried and evaporated to give a brown solid (0.95 g, 73%) whose structure was confirmed by NMR and mass spectroscopy.

Provenance & Evidence