benzyl 4-(1H-indol-3-yl)butanoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of benzyl 4-(3-indolyl)butyrate (33.70 g) in dichloromethane (400 ml) were added triethylamine (30 ml), 4-dimethylaminopyridine (1.22 g) and 3-nitrobenzoyl chloride (30.0 g). After refluxed for 16 hours, 3-nitrobenzoyl chloride (10.5 g) and triethylamine (5 ml) were added to the mixture. The mixture was allowed to reflux for 19 hours and 3-dimethylaminopropylamine (15 ml) was added at 0° C. The mixture was washed with diluted hydrochloric acid (200 ml ×2) and water (200 ml×4) and dried over magnesium sulfate. The solvent was removed in vacuo to give a solid of benzyl 4-[1-(3-nitrobenzoyl)indol-3-yl]butyrate (47.61 g). After refluxed for 16 hours to reflux for 19 hours The mixture was washed with diluted hydrochloric acid (200 ml ×2) and water (200 ml×4) dried over magnesium sulfate The solvent was removed in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-indolebutyric acid (25 g) and potassium carbonate (20 g) in dimethylformamide (150 ml) was added benzylbromide (21 g) at room temperature. After stirring for 4 hours, the mixture was poured into ice and diluted hydrochloric acid (300 ml). The organic layer was extracted with ethyl acetate (150 ml), and the extract was washed with water (150 ml×3) and dried over magnesium sulfate. After the solvent was removed in vacuo, the residue was crystallized from n-hexane to give a solid of benzyl 4-(3-indolyl)butyrate (33.9 g). The organic layer was extracted with ethyl acetate (150 ml) the extract was washed with water (150 ml×3) dried over magnesium sulfate After the solvent was removed in vacuo the residue was crystallized from n-hexane