5-Decyne → Cis-5-Decene

To a solution of rhodium(III) chloride trihydrate (1.3 mg, 0.005 mmol), copper(II) nitrate hemipentahydrate (2.90 mg, 0.0125 mmol) and aluminum(III) nitrate nonahydrate (0.188 g, 0.50 mmol) in a mixture of THF (2.5 mL) and water (0.5 mL) is added 5-decyne (69 mg, 0.50 mmol). The solution is stirred for 10 minutes and then triethoxysilone (0.21 g, 1.25 mmol) is added. The system is closed and stirred at room temperature for 7 hours. The volatiles are removed in vacuo. A mixture of hexane (5 mL) and ether (1 mL) is added. The solution is dried over magnesium sulfate and filtered through a one inch plug of silica gel. The substrate is eluted with hexane/ether (5:1). The solvent is removed in vacuo to give Z-5-decene.

1. additiontriethoxysilone (0.21 g, 1.25 mmol) is added
2. customThe system is closed
3. stirringstirred at room temperature for 7 hours
4. customThe volatiles are removed in vacuo
5. additionA mixture of hexane (5 mL) and ether (1 mL)
6. additionis added
7. dry with materialThe solution is dried over magnesium sulfate
8. filtrationfiltered through a one inch plug of silica gel
9. washThe substrate is eluted with hexane/ether (5:1)
10. customThe solvent is removed in vacuo

ORD-Eintrag

ord-ca2947be9dd4451289a37022955c91f9

Quelldatensatz

uspto-grants-1996_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05492964