undec-2-yn-1-ol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 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## Hydrogen was bubbled through the reaction mixture The reaction mixture was filtered the filtrate was concentrated by rotary evaporation

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 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## Hydrogen was bubbled through the reaction mixture The reaction mixture was filtered the filtrate was concentrated by rotary evaporation

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of tetrahydro-2-(2-undecynyloxy)-2H-pyran in methanol (100 mL), was added p-toluenesulfonic acid (30 mg). The mixture was stirred at room temperature for 4 hours. The solvent was removed by rotary evaporation. The residue was taken up in ether (150 mL) and washed with aqueous saturated NaHCO3 (120 mL), saturated NaCl (120 mL) and water (200 mL). The organic layer was dried (MgSO4) and concentrated to yield a yellow oil. Purification by flash silica gel chromatography (90:10 hexane/EtOAc) afforded 2-undecyn-1-ol (48) (2.6 g, 77% overall) as a colorless oil: Rf 0.27 (90:10 hexane/EtOAc); IR (neat) 3300, 2925, 2855, 1437, 1110 Cm-1 ; 1H NMR (CDCl3) δ 4.18 (t, J=2.4 Hz, 2 H), 2.8 (s, 1 H), 2.14 (tt, J1 =7.2 Hz, J2 =2.4 Hz, 2 H), 1.35 (m, 12 H), 0.82 (t, J=6.9 Hz, 3 H); 13C NMR (CDCl3) δ 86.15, 78.28, 50.93, 31.76, 29.09, 29.04, 28.82, 28.56, 22.56, 18.63, 13.95. ##STR22## The solvent was removed by rotary evaporation washed with aqueous saturated NaHCO3 (120 mL), saturated NaCl (120 mL) and water (200 mL) The organic layer was dried (MgSO4) concentrated to yield a yellow oil Purification by flash silica gel chromatography (90:10 hexane/EtOAc)