1,3-Propanediamine → Pentadec-14-yn-1-ol

Participants

Reaction Steps

The same procedure for 8-nonyn-1-ol was followed with 2- pentadecyn-1-ol (4.51 g, 20.1 mmol), KH (2.38 g, 59.4 mmol), and 1,3-diaminopropane (65 mL). This produced 3.18 g of white solid (70%): mp 42-44° C. IR (thin film( ν 3430, 2926, 2252 cm−1: 1H—NMR δ4.30 (t, 1H, J=5.0 Hz), 3.64 (t, 2H, J=6.6 Hz), 2.18 (td, 2H, J=2.6 Hz, 6.6 Hz), 1.94 (t, 1H, J=2.6 Hz), 1.49-1.26 (bm, 22H); 13C—NMR δ 84.8, 68.0, 63.1, 32.8, 29.6, (2C), 29.5 (2C), 29.4, 28.9, 28.5, 28.7, 28.0, 25.7, 18.4; MS m/z 231.53 (M++Li). Anal. Calcd for C15H28O: C, 80.29; H, 12.58. Found: C, 18.20; H, 12.50.

Provenance & Evidence