mol 24 6 ml in anhydrous ether 50 ml was added a solution of 7 ethyl 1h indole 7 25 g 0 05 mol in benzene 25 ml dropwise over the course of 10 minutes the resulting pale green mixture was heated at reflux for 2 hours and then cooled to 10 u00b0 c with a dry ice methanol bath a solution of hydrocinnamoyl chloride 8 43 g 0 05 mol in benzene 20 ml was added dropwise 45 minutes the reaction mixture was allowed to warm to room temperature after an additional 2 hours no starting material was detected by tlc analysis aqueous ammonium chloride 10 30 ml was added to the reaction mixture and a white precipitate formed which was collected by filtration washed with ether and dried in vacuo to yield 7 78 g 56 of the desired ketone m p 140 u00b0 141 5 u00b0 c nmr cdcl 3 u03b4 9 39 s 1h 8 30 d 1h 7 80 d 1h 3 12 s 4h 2 88 q 2h 1 32 t 3h according to the procedure of e c taylor et al j amer chem soc 98 3037 1976 a solution of 1 7 ethyl 1h indol 3 yl 3 phenylpropanone 2 77 g 10 mmol in a 1 1 mixture of methanol and trimethylorthoformate 25 ml.