Quinoline → 2-Decen-1-ol, (Z)-

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).

1. customthe flask was evacuated (house vacuum, ca. 50 mm Hg)
2. customflushed with H2 three times
3. waitleft under a H2 atmosphere
4. customThe catalyst was removed by filtration through a 4 cm pad of celite
5. washthe filtrate was washed two times with 100 ml of 1N HCl
6. dry with materialonce with 100 ml of saturated NaHCO3, once with 100 ml of brine, dried over MgSO4
7. filtrationfiltered
8. customthe solvent evaporated
9. customto give a pale yellow oil
10. distillationKugelrohr distillation (100°-120° C. oven, 0.2 mm)

ORD record

ord-df19c5af3dec4a66940df3e8e148c7d2

Source dataset

uspto-grants-1993_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05190969