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In a round-bottom flask equipped with a stir bar and under an atmosphere of argon was added KH (4.46 g, 111 mmol). The flask was cooled to 0° C. and 1,3-diaminopropane (50 mL) was added slowly via syringe. The solution was stirred for 45 min. Then 2-nonyn-1-ol, dissolved in of 1,3-diaminopropane (30 mL), was added dropwise via syringe to the stirring solution. The reaction was stirred for an additional 30 min at 0° C. before warming to room temperature overnight. The reaction was again cooled to 0° C. before quenching with water. The compound was extracted with Et2O, washed with HCL, water, and brine, dried with MgSO4, and concentrated. This produced 4.94 g of dark orange oil which was purified by flash column chromatography on silica gel (2.5% Et2O in hexane to 50% Et2O in hexane) to give 3.21 g of clear oil (67%): IR (near) ν 3409, 2931, 2242 cm−1, 1H—NMR δ 3.59 (t, 2H, J=7.0 Hz), 2.14 (td, 2H, J=3.0 Hz, 7.0 Hz), 2.10 (s, 1H), 1.91 (t, 1H, J=3.0 Hz), 1.50 (bm, 4H), 1.30 (bm, 6H); 13C—NMR δ 84.6, 68.1, 62.8, 32.6, 28.8, 28.6, 28.3, 25.6, 18.3; MS m/z 147.10 (M++Li). Anal. Calcd for C9H16O: C, 77.09; H, 11.46. Found: C, 77.00; H, 11.46.

1. customIn a round-bottom flask equipped with a stir bar and under an atmosphere of argon
2. additionwas added KH (4.46 g, 111 mmol)
3. additionwas added dropwise via syringe to the stirring solution
4. stirringThe reaction was stirred for an additional 30 min at 0° C.
5. temperaturebefore warming to room temperature overnight
6. temperatureThe reaction was again cooled to 0° C.
7. custombefore quenching with water
8. extractionThe compound was extracted with Et2O
9. washwashed with HCL, water, and brine
10. dry with materialdried with MgSO4
11. concentrationconcentrated
12. customThis produced 4.94 g of dark orange oil which was purified by flash column chromatography on silica gel (2.5% Et2O in hexane to 50% Et2O in hexane)