CC1C=CC(S(O[CH2:12][CH2:13][C:14]#[CH:15])(=O)=O)=CC=1.[CH2:16]([NH:18][CH2:19][CH3:20])[CH3:17].O1CCOCC1>C(OCC)C>[CH2:16]([N:18]([CH2:19][CH3:20])[CH2:12][CH2:13][C:14]#[CH:15])[CH3:17]Prepared using methodology described by Olomucki, M., et al. Ann. Chim. 1960, 5, 845. A stirred mixture of but-3-ynyl 4-methylbenzenesulfonate (21.2 g, 94.5 mmol), diethylamine (6.91 g, 94.5 mmol), and p-dioxane (100 mL) was heated to 80° C. under N2 for 6 hours. After cooling to room temperature, the suspension was diluted with diethyl ether (100 mL) and filtered. The solids were washed with diethyl ether (50 mL). The filtrate was concentrated to a brown oil. The crude was co-distilled (55-65° C.) with p-dioxane under a mild vacuum (10-50 torr). The product was obtained as an oil (7.6 g, 27%), in a 42:58 mixture with p-dioxane based on 1H NMR. 1H NMR (400 MHz, CDCl3) δ 2.70 (t, J=8 Hz, 2H), 2.55 (q, J=7 Hz, 4H), 2.32 (m, 2H), 1.97 (t, J=3 Hz, 1H), 1.04 (t, J=7 Hz, 6H).
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