Indole-3-Carboxaldehyde → HCID 54364322, compound

Participants

Reaction Steps

A suspension of 10.6 g. (0.44 mole) of sodium hydride in 50 ml. of dry dimethylformamide is treated dropwise with a solution of 58 g. (0.40 mole) of indole-3-carboxaldehyde in 200 ml. of dimethylformamide. An exothermic reaction is observed with the temperature rising to 70° C. The resulting mixture is stirred for one hour. To the resulting mixture there is added 69 g. (0.42 mole) of 2-methyl-2(3-chloropropyl)-dioxolane, and the mixture is maintained overnight at room temperature. The solvent is evaporated and the residue is extracted with ether, washed with water and dried over anhydrous magnesium sulfate. Following the evaporation of the solvent, the residue is crystallized from ether/hexane to give 1-[3-(2-methyl-2-dioxolanyl)propyl]-3-indolecarboxaldehyde, m.p. 52°-55° C.

Provenance & Evidence