CC1C=CC(S([O:11][CH2:12][CH2:13][C:14]#[CH:15])(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+].[CH2:22]([NH:24][CH2:25][CH3:26])[CH3:23]>C1COCC1>[CH2:22]([N:24]([CH2:25][CH3:26])[CH2:12][CH2:13][C:14]#[CH:15])[CH3:23].[CH2:14]1[CH2:15][O:11][CH2:12][CH2:13]1A mixture of 3-butynyl 4-methylbenzenesulfonate (10 mL, 57 mmol), K2CO3 (7.9 g, 57 mmol), and diethylamine (23.5 mL, 228 mmol) in 100 mL of THF was heated to reflux for 31 hours, cooled to room temperature, and filtered. The filtrate was concentrated under vacuum at a distillation temperature of 60° C. to provide 11.2 g of a 53 wt % solution of the desired product in THF (5.9 g assay, 83% yield). 1H NMR (400 MHz, DMSO-d6) δ 0.93 (t, J=7.07 Hz, 6H) 2.21 (m, 2H) 2.44 (q, J=7.04 Hz, 4H) 2.55 (m, 2H) 2.72 (t, J=2.68 Hz, 1H).
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