Sodium hydride → HCID 18973467, compound

Participants

Reaction Steps

Sodium hydride (95%; 0.30 g) was suspended in 10 ml of dimethylformamide and the suspension was stirred while cooling the same at a temperature ranging from 0° to 5° C. To this mixed liquid, there was dropwise added a solution of 2.00 g of methyl indole-4-carboxylate in 5 ml of dimethylformamide over 15 minutes. After the completion of the dropwise addition, the reaction solution was stirred at a temperature ranging from 0° to 5° C. for 30 minutes. To the reaction solution, there was added a solution of 2.09 g of 4-ethylbenzoyl chloride in 5 ml of dimethylformamide, followed by stirring at room temperature for 2 hours. The reaction solution was poured into 200 ml of a 10% ammonium chloride aqueous solution, followed by extraction with ethyl acetate (200 ml×2). The extract was washed with a saturated common salt solution, dried over anhydrous sodium sulfate and the solvent was removed through distillation under reduced pressure to thus give 3.51 g of a residue. The residue was purified by silica gel chromatography (hexane:ethyl acetate=11:1) to give 2.18 g of methyl 1-(4-ethylbenzoyl)indole-4-carboxylate as colorless crystals. The yield thereof was found to be 62%.

Provenance & Evidence