3-Octyn-1-ol → 7-Octyn-1-ol

Participants

Reaction Steps

The same procedure for 8-nonyn-1-ol was followed with 3-octyn-1-ol (6.89 g, 54.6 mmol), KH (6.57 g, 16.4 mmol), and 1,3-diaminopropane (60 mL). This produced 6.09 g of clear yellowish liquid (88%): IR (neat)ν 3360, 2896, 2116 cm−1; 1H—NMR δ 3.44 (t, 2H, J=6.6 Hz), 3.27 (bs, 1H), 2.04 (td, 2H, J=2.6 Hz, 6.6 Hz), 1.83 (t, 1H, J=2.6 Hz), 1.39 (m, 4H), 1.25 (m, 4H); 13C NMR δ 84.5, 68.3, 62.2, 32.3, 28.3, 25.2, (2C), 18.2; MS m/z 136.00 (m++Li). Anal. Calcd for C8H14O: C, 76.14; H, 11.18. Found: C, 76.04; H, 11.16.

Provenance & Evidence