Indole-3-Acetic Acid → Ethyl 4-(3-indolyl)-3-oxobutyrate

Participants

Reaction Conditions

Reaction Steps

24.95 g (154 mmol) of carbonyldiimidazole are added at 0° C. to a solution of 24.5 g (140 mmol) of 3-indolyl-acetic acid in 250 ml of tetrahydrofuran and the mixture is stirred at 0° C. for 30 minutes. 46 g (161 mmol) of bis-(malonic acid monoethyl ester)magnesium salt are then added and the mixture is stirred at room temperature for 16 hours. The reaction mixture is concentrated by evaporation, and ice-cold 6N hydrochloric acid is added; diethyl ether is added and the organic phase is separated off. The organic phase is washed with aqueous 10% sodium hydrogen carbonate solution and brine, dried over magnesium sulfate and concentrated by evaporation. The title compound is obtained in the form of an orange oil. 1H-NMR (200 MHz): 8.22 (br. s, 1H), 7.53 (d, 1H), 7.37 (d, 1H), 7.28-7.10 (m, 3H), 4.23 (q, 2H), 3,93 (s, 2H), 3.46 (s, 2H), 1.22 (t, 3H).

Provenance & Evidence