generated the ylid followed by subsequent olefination of the ketone the reaction was slowly warmed to room temperature over 2 h and then stirred at 75 u00b0 c for 1 h the solution was partitioned between etoac nh 4 cl dried over na 2 so 4 evaporated and purified by silica gel chromatography 2 etoac hexanes yielding 2 5 g 55 of enol ether 9 as an oil 1 h nmr ppm 1 55 1 95 12h m 2 61 1h br s 3 21 1h br s 3 28 3h s 3 78 3h s 6 74 1h s 6 80 1h s 6 87 1h s demethylation to enol ether phenol 10 proceeded cleanly upon heating enol ether 9 2 5 g 7 8 mmol in dmf 14 ml at 155 u00b0 c in the presence of sodium ethane thiolate 11 7 mmol upon cooling the mixture was partitioned between etoac and nh 4 cl dried over na 2 so 4 and evaporated under high vacuum to remove residual dmf chromatographic purification silica gel 20 etoac hexanes produced 2 3 g 96 of phenol 10 as an oil which crystallized upon standing trituration of the solid with 5 etoac hexanes gave white crystals mp 133 u00b0 c ir chcl 3 cm u2212 1 3584 oh 3300 oh 2910 1590 1310 1285 1163 1096 1080 1011 900 840 1 h nmr ppm 1 73 1 96 12h m 2 62 1h br s 3 20 1h br s 3 32 3h s 5 65 1h br s 6 73 1h s 6 79 1h m 6 85 1h s triethylamine 450.