j 2 7 hz 1h 7 07 t j 8 1 hz 1h 6 94 d j 8 1 hz 1h 6 73 6 75 m 1h 4 28 4 38 m 4h 1 23 t j 7 1 hz 6h anal calcd for c 15 h 16 brno 5 c 48 76 h 4 36 n 3 79 found c 48 79 h 4 43 n 3 61 the more polar compound was diethyl 2 indol 4 yloxy malonate 8 as white crystals 260 mg 45 mp 52 53 u00b0 c from diethyl ether hexanes 1 h nmr 500 mhz u03b4 8 25 br s 1h 7 13 dd j 3 1 2 6 hz 1h 7 09 d j 7 8 hz 1h 7 05 t j 7 8 hz 1h 6 76 6 77 m 1h 6 50 d j 7 5 hz 1h 5 35 s 1h 4 28 4 37 m 4h 1 30 t j 7 1 hz 6h anal calcd for c 15 h 17 no 5 c 61 85 h 5 88 n 4 81 found c 61 91 h 6 17 n 4 68 ii a solution of 4 hydroxyindole 266 mg 2 mmol in acetone 20 ml was cooled to 0 u00b0 c under nitrogen and anhydrous potassium carbonate 414 mg 3 mmol was added a solution of commercial diethyl bromomalonate 92 520 mg 2 mmol in acetone 20 ml was added dropwise after stirring for 5 h at room temperature more diethyl bromomalonate 92 520 mg was added and the mixture was stirred at room temperature overnight work up and flash chromatography as above afforded 7 360 mg 45 and 8 123 mg 21 iii a solution of 4 hydroxyindole 266 mg 2 mmol in acetone.