the phenolate salt did not exhibit a melting point below 280 u00b0 but did darken somewhat beginning at 170 u00b0 it was kept dry during all subsequent manipulations and stored in a dessicator over drierite ir nujol mull 1572 1405 1310 1285 1198 1175 1150 1090 988 870 800 777 cm 1 sodium 3 methoxytricyclo 3 3 1 1 3 7 dec 2 ylidenemethyl phenoxide 1 74 g 6 0 mmol was added under argon to 10 ml of scrupulously dried dimethylformamide containing several drops of triethylamine the resulting slurry was vigorously swirled during the addition of 2 chloro 2 oxo 1 3 2 dioxaphospholane 0 580 ml 6 3 mmol over 25 minutes the mixture thinned considerably during this addition and over an additional 3 5 hours of vigorous stirring at room temperature dry sodium cyanide 0 325 g 6 6 mmol was then added with exclusion of moisture and stirring was continued overnight at room temperature to give an orange cloudy solution the solvent was removed in vacuo 1 0 mm hg at 50 u00b0 and the residue was chased twice with o xylenes to further eliminate dmf the resulting brown foam was dissolved in 10 ml of methanol prior to the dropwise addition of 4 37m sodium methoxide in methanol 1 30 ml 5 7 mmol after 30 minutes the solvent was removed on the rotory evaporator and the residue was slurred in 5 water acetone v v and filtered the solid filter cake was dissolved in water and subjected to reverse phase chromatography plrp polystyrene.