Quinoline → 2-Decen-1-ol, (Z)-

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To a solution of 10.0 g of 2-decyn-1-ol in 150 ml petroleum ether was added 500 mg of Pd on CaCO3 poisoned with lead (Lindlar catalyst). Quinoline (2.0 ml) was then added to this mixture and the flask was evacuated (house vacuum, ca. 50 mm Hg) and flushed with H2 three times and left under a H2 atmosphere. The mixture was stirred vigorously until uptake of H2 was no longer evident and TLC (SiO2 /20% ether:pet. ether) showed no starting material. The catalyst was removed by filtration through a 4 cm pad of celite and the filtrate was washed two times with 100 ml of 1N HCl, once with 100 ml of saturated NaHCO3, once with 100 ml of brine, dried over MgSO4, filtered and the solvent evaporated to give a pale yellow oil. Kugelrohr distillation (100°-120° C. oven, 0.2 mm) affords 8.81 g of clear oil. 1H NMR δ 5.57 (m,2), 4.20 (t, 2, J=5 Hz), 2.07 (dd, 2, J=6, 12 Hz), 1.5-1.1 (m, 10), 0.88 (t, 3, J=7 Hz).

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