C(N(CC)CC)C.[S:8](/[CH:11]=[CH:12]\[C:13]([OH:15])=[O:14])[C:9]#[N:10].CS(Cl)(=O)=O.[C:21]1(O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CN(C1C=CC=CN=1)C.[K+].[Br-]>C1(C)C=CC=CC=1.C(Cl)Cl.O>[S:8](/[CH:11]=[CH:12]\[C:13]([O:15][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:14])[C:9]#[N:10]Triethylamine (2.3 g., 0.031 mole) in 5 ml of dry toluene was added dropwise to a stirred suspension of compound 2 (4.0 g., 0.031 mole) in 30 ml of dry toluene at 0° C. To the resulting solution, methanesulfonyl chloride (3.55 g., 0.031 mole) in 15 ml of dry toluene was added dropwise at 0° C. and stirred for 30 minutes. A solution of phenol (2.9 g., 0.031 mole) and dimethylaminopyridine (DMAP) (3.5 g., 0.028 mole) in 40 ml of dry toluene was added dropwise with stirring at 0° C. The mixture was allowed to warm to room temperature and stirred for an additional 3 hours. The mixture, consisting of yellowish gum in a two-phase mixture with toluene, was diluted with methylene chloride, poured into water and the organic phase was separated. The aqueous phase was extracted with methylene chloride. The combined organic phase was washed with sodium bicarbonate solution, water, dried (MgSO4) and concentrated. The residue was column-chromatographed on silica gel using hexane/ether (4:1) as eluant to give product as white crystals, 2.9 g: mp 79°-83° C.; IR (KBr) 1700, 2175 cm-1.
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