Diethyl Ether → ethyl 1-(4-chlorobenzyl)-3-methyl-1H-indole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

Ethyl 3-methyl-1H-indole-2-carboxylate (480 mg, 2.362 mmol) was dissolved in anhydrous DMF (5 mL), followed by the addition of granular potassium carbonate (408 mg, 2.95 mmol) and p-chlorobenzylchloride (0.38 mL, 2.95 mmol). The reaction was allowed to stir at 60° C. for 24 h, after which time the solution was diluted with a 1:1 solution of ethyl acetate:diethyl ether. The organic phase was washed with 10% aqueous sodium carbonate, dried with magnesium sulfate, and concentrated in vacuo. Purification was accomplished via silica gel flash chromatography (60 g silica, 10% EtOAc/hexanes) to give the title compound as a white powder. (Yield: 510 mg, 1.60 mmol, 66%) 1H NMR (400 MHz, CDCl3) 7.71, 7.34-7.15, 6.95, 5.73, 4.34, 2.63, 1.36

Provenance & Evidence