[OH-].[Na+].O.[CH2:4]([OH:7])[C:5]#[CH:6].[CH2:8](Br)[CH2:9][CH2:10][CH2:11][CH3:12]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC>[CH2:8]([O:7][CH2:4][C:5]#[CH:6])[CH2:9][CH2:10][CH2:11][CH3:12]To a 500 mL 3 neck flask equipped with magnetic stirrer, addition funnel, and thermometer was charged 140 grams (g) of 50% sodium hydroxide in water (1.75 mol), 1.88 g of tetrabutyl ammonium bromide (5.83 mmol), and 120 mL of dry hexane. The reaction mixture was stirred rapidly at ambient temperature followed by the dropwise addition of 13 g (0.232 moles) of propargyl alcohol and 43.16 ml (0.35 moles) of n-pentyl bromide. The reaction was refluxed for 3 hours, after which two phases formed when agitation was stopped. The upper (organic) phase was collected via a separatory funnel, and this material was distilled at atmospheric pressure. The purest fractions were combined to afford 28.2 g of a clear pale yellow liquid which was consistent with the target molecule upon analysis by 1H NMR. The NMR data is as follows: 300 MHz 1H NMR (CDCl3, TMS=0 ppm) 0.95 (m, 3H); 1.33 (m, 4H); 1.55 (m, 2H); 2.40 (s, 1H); 3.50 (m, 2H); 4.15 (s, 2H).
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