11-Dodecyn-1-ol is a synthetic intermediate of the sex pheromone (Z,E)-11,13,15-Hexadecatrienyl acetate for Thaumetopoea processionea[1].
NaH (7.5 g, 60% oil dispersion, 326 mmol) was added batchwise to a stirred 0 C solution of dodeca-3-yn-1-ol (10.0 g, 54.95 mmol; GF Smith) in ethylenediamine (40 mL).After 1 h, the temperature was raised to 70 C. The reaction mixture was cooled to 0 C for another 8 h and carefully terminated with ice-cold water (100 mL) and extracted with ether (3 x 60 mL). After another 8h, the reaction mixture was cooled to 0 C, carefully terminated with ice-cold water (100 mL) and extracted with ether (3 x 60 mL). The combined ether extracts were washed with water (100 mL). The aqueous washings were back-extracted with ether (3 x 60mL). The combined organic extracts were concentrated under vacuum and the residue was subjected to column chromatography using 10% EtOAc/hexane to obtain 11-dodecyne-1-ol (7.4 g, 74%) contaminated with 3-5% of other regioisomers (regioisomer).TLC: 30% EtOAc/hexane, Rf 0.4; 1H NMR (300 MHz, CDCl3). CDCl3) 3.66 (t, 2H, J = 7.3 Hz), 2.14-2.21 (m, 2H), 1.93 (t, J = 1.9 Hz, 1H), 1.20-1.63 (m, 16H).
[1] Gries R, et al. (Z, Z)-11, 13-Hexadecadienyl acetate and (Z, E)-11, 13, 15-hexadecatrienyl acetate: synergistic sex pheromone components of oak processionary moth, Thaumetopoea processionea (Lepidoptera: Thaumetopoeidae)[J]. Chemoecology, 2004, 14: 95-100...
