1,8-Nonadiyne → HCID 85962992, compound

Participants

Reaction Steps

Pyrollidine (20 mL) and CuI (0.65 g, 3.42 mmol) were added to a nitrogen flushed reaction vessel. Nona-1,8-diyne (1.58 g, 13.17 mmol) was added via syringe. 1-Iodo-1decyne (2.26 g, 8.53 mmol) was added via syringe dropwise to the solution over ten minutes. The reaction was stirred under nitrogen for 24 h. The reaction mix was then quenched with ammonium chloride (10 mL), separated with diethyl ether, and dried with anhydrous magnesium sulfate. Nonadeca-1,8,10-triyne was then isolated using silica column chromatography with a 1% ether/hexane eluting solution obtaining 1.06 g of an oil. 50% yield; 1H NMR (CDCl3) δ 2.29 (m, 4H, CH2—C≡C), 2.22 (dt, 2H, CH2—C≡C, J=7, 2.7 Hz), 1.97 (t, 1H, H—C≡C, J=2.7 Hz), 1.54 (m, 6H, CH2—C—C≡C), 1.33-1.40 (sextuplet, 2H, CH2—CH2—CH3), 1.27 (m, 10H, C—CH2—C), 0.88 (t, 3H, CH3); 13C NMR (CDCl3) δ: 84.62, 77.99, 77.36, 68.63, 65.76, 65.45, 32.21, 29.54, 29.46, 29.25, 28.72, 28.34, 28.31, 28.23, 23.06, 19.61, 19.52, 14.53; MS (ESI) [M+Na]+ calc. 279.2083 found 279.1723 (very unstable to any MS technique). Elemental analysis calc. for C19H28: C, 88.99; H, 11.01. Found: C, 88.80; H, 10.96.

Provenance & Evidence