[CH2:1]([OH:6])[C:2]#[C:3][CH2:4][CH3:5].[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1.[OH-].[K+]>C1COCC1.[Cl-].[Na+].O>[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13]([O:6][CH2:1][C:2]#[C:3][CH2:4][CH3:5])(=[O:15])=[O:14])=[CH:9][CH:8]=1A solution of 2-pentyn-1-ol (8.40 g, 100 mmol) in THF (60 mL) was treated with p-toluenesulfonyl chloride (23.9 g, 125 mmol) at -10° C., followed by pulverized KOH (11.3 g, 200 mmol) without allowing the temperature to exceed -5° C. After 1.5 hours of stirring at -10° C., 50 mL of saturated brine was added and the product extracted into CH2Cl2. The product, 2-pentyn-1-yl p-toluenesulphonate (2), was isolated by flash chromatography (18.17 g 76.4% yield). 1H NMR (200 MHz) δ: 7.81 (d, J=8.4 Hz, 2H, arom. CH), 7.33 (d, J=7.9 Hz, 2H, arom. CH), 4.68 (t, J=2.2, 2.2 Hz, 2H, CH2O-1), 2.44 (s, 3H, arom. CH3), 2.13 (tq, J=2.2, 2.2, 2.2, 7.5, 7.5 Hz, 2H, CH2 -4), 1.00 (t, J=7.5, 7.5 Hz, 3H, CH3 -5).
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