1H-Indole-3-propanoic acid → 3-(1H-Indol-3-yl)propanoic acid cyanomethyl ester

Participants

Reaction Steps

3-(1H-Indol-3-yl)propanoic acid (5 g, 26 mmol) was dissolved in acetone (50 ml), and caesium carbonate (4.2 g, 13.0 mmol), chloroacetonitrile (1.8 ml, 28.6 mmol) and potassium iodide (20 mg) were added in succession. After a reaction time of 3 d at room temperature with exclusion of moisture, the solid residues were separated off by filtration and the filtrate was concentrated. The crude product of the ester was obtained only in a yield of 3.6 g by this procedure. The filtrate was taken up again in acetone (25 ml) and, for better solubility of the caesium salt formed as an intermediate product, DMF (25 ml) was added. The residue separated off previously, chloroacetonitrile (1.8 ml, 18.6 mmol) and potassium iodide (20 mg) was added to this solution. The reaction mixture was stirred at 60° C. for 3 h and at room temperature for 16H, with exclusion of water. The solid residues was separated off by filtration and the filtrate was concentrated. It was possible to obtain further crude product of the ester, which still contained DMF. The two crude products were combined and purified by chromatography on silica gel with ethyl acetate/cyclohexane (1:3). The desired cyanomethyl ester was obtained as a beige-coloured compound with a melting point of 72° C. in a yield of 91% (5.36 g).

Provenance & Evidence