2-Pentadecyn-1-ol → Pentadec-14-yn-1-ol

Participants

Reaction Steps

Isomerization of pentadec-2-yn-1-ol (12.5 g, 54.95 mmol) using NaH/ethylenediamine as described above furnished pentadec-14-yn-1-ol (9.4 g, 76%) as a white solid. M.P.: 54.2-54.8° C. TLC: 30% EtOAc/hexanes, Rf≈0.45; 1H NMR (400 MHz, CDCl3) δ 3.60-3.65 (m, 2H), 2.16 (dt, 2H, J=7.1 Hz, 2.4 Hz), 1.92 (t, 1H, J=2.4 Hz), 1.47-1.60 (m, 4H), 1.22-1.35 (m, 18H).

Provenance & Evidence