NaH (60% mineral oil suspension, 17.1 g, 42.8 mmol, 4 eq.) was carefully added in batches to a flask containing pure anhydrous ethylenediamine (70 mL) at 0 C. The mixture was slowly warmed to room temperature and stirred at room temperature for 1 hr, then warmed to 70 C. After 2 hr, the reaction mixture was cooled to 45 C and commercially available 2-nonyl-1-ol (35) (15 g, 10.71 mmol) was slowly added. After stirring at 70 C for 5 h, the reaction mixture was cooled to 0 C and slowly quenched with 1MHCl (30 mL) to separate the organic and aqueous layers. The aqueous layer was extracted with Et2O (2 x 120 mL). The ether extract was combined with the organic layer, dried (Na2SO4), and all volatiles were removed under reduced pressure. The residue was purified by SiO2 column chromatography using 20% EtOAc/hexane to afford 8-nonyn-1-ol (36) (4.1 g, 82%) as a colorless oil
