Undec-2-yn-1-ol → 2-Undecen-1-ol, (2Z)-

Participants

Reaction Steps

To a solution of 2-Undecyn-1-ol (48) (0.5 g, 3 mmol) in EtOAc (10 mL) was added Lindlar catalyst (25 mg). Hydrogen was bubbled through the reaction mixture. After 2 hours, the reaction was judged complete by TLC (90:10 EtOAc/Petroleum ether, Rf (13)=0.61, Rf (14)=0.55). The reaction mixture was filtered and the filtrate was concentrated by rotary evaporation to yield cis-2-Undecen-1-ol (14) as a colorless oil: 1H NMR (CDCl3) δ 5.60 (m, 2 H), 4.21 (s, 2 H), 2.14 (m, 2 H), 1.35 (m, 12 H), 0.82 (t, J=6.9 Hz, 3 H); 13C NMR (CDCl3) δ 132.98, 128.32, 58.42, 31.85, 29.57, 29.29, 29.19, 27.38, 22.63, 14.04. ##STR23##

Provenance & Evidence