50 8 ml 127 2 mmol was added and the mixture was stirred for sixty minutes after this time zncl 2 1 0 m in ether 127 2 ml 127 2 mmol was added slowly giving a white precipitate next the reaction mixture was allowed to slowly warm to room temperature and was then refluxed for four hours following the reflux period the reaction mixture was cooled to room temperature and pd pph 3 4 1 85 g 1 6 mmol was added followed by the slow addition of dimethyl malonyl chloride 2 0 ml 15 1 mmol after completion of the additions the reaction mixture was brought to reflux and stirred overnight after this time the reaction mixture was poured into 500 ml saturated aqueous sodium bicarbonate the two phase mixture was filtered and separated the organic phase was washed with brine and dried over sodium sulfate the solvent was removed by rotary evaporation to give a pale orange solid this solid was dissolved in a minimal amount of acetone and passed through a short plug of silica gel using hexanes as the eluent upon removal of the solvent a pale yellow solid was obtained this material was recrystallized from hexanes to give pale yellow needles yield 3 7 g 23 mp 159 162 u00b0 c 1 h nmr cdcl 3 u03b4 7 54 m 4h 6 99 dd 2h j 5 0 4 0 hz 1 69 s 6h ir kbr pellet cm u2212 1 3114 4 3099 0 2994 1 2932 5 1663 3 1636 2 1512 9 1461 1 1408 0 1352 6 1268 8 1254 0 1241 7 1172 6 1054 3 965 5 903 9.