[O:1]1CCCC1.S(=O)(=O)(O)O.[OH:11][C:12]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH:15]([CH3:17])[CH3:16])[C:13]#[CH:14]>O>[OH:11][C:12]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([CH:15]([CH3:17])[CH3:16])[C:13](=[O:1])[CH3:14]To a refluxing mixture of tetrahydrofuran (70 ml), water (5 ml), and conc. sulfuric acid (1.5 g) is added 1 g of red mercuric oxide and the reflux is continued for 5 min. Then, the inside temperature is adjusted to 60°-62° C. and 10 g of 3-hydroxy-4-methyl-3-phenyl-1-pentyne (described in Example 1) is added. The reaction is exothermic (spontaneous mild reflux) and there is a noticeable clearing of the mixture. Another 1 g of mercuric oxide is added, and the solution is refluxed for 30 min. The reaction mixture is stirred at 60° C. for an additional 3 hr, during which time the precipitation of a mercury sludge occurred. After cooling, the slurry is diluted with 100 ml of diethyl ether and filtered through diatomaceous earth. The filter cake is washed with 200 ml of diethyl ether, and the combined filtrates are washed repeatedly with water, dried over magnesium sulfate, filtered, and evaporated to give 10.6 g of the title product, ir (CDCl3) 3470 and 1715-1710 cm-1 and nmr (CDCl3) δ 0.91(d), 2.15(s), 2.79(heptuplet), 4.39(s) and 7.20-7.65(m).
Wird geladen…
