[Br:1][CH:2]([OH:5])[C:3]#[CH:4].[OH-].[Na+].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>O.O1CCCC1>[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14]([O:5][CH:2]([Br:1])[C:3]#[CH:4])(=[O:16])=[O:15])=[CH:10][CH:9]=1In a 100 mL 3-necked round bottom flask, equipped with a magnetic stirrer, nitrogen inlet, thermometer, addition funnel, and ice bath, were placed bromopropargyl alcohol (5 g, 0.037 mole) and tetrahydrofuran (10 mL). A cold solution of NaOH (2.2 g, 0.55 mole) in water (10 mL) was added. To the above stirred mixture a solution of p-toluenesufonyl chloride (7.06 g, 0.037 mole) in tetrahydrofuran (10 mL) was slowly added. The reaction mixture was stirred at 0°-5° C. for 4 hrs. The reaction mixture was then poured into ice water and the resultant white precipitate was collected by suction-filtration and washed with water. After drying in air, an off-white solid was obtained yielding 9.9 g (92.5% yield) m.p. =43°-46° C. An NMR (CDCl3) spectrum indicated the desired compound (V, R3 =p-tolyl). This compound is used in the next example without further purification.
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