Water → Cis-5-Decene

HRID 728009

Reaktionsgleichung

Reaktionsgleichung von HRID 728009
O.[CH3:2][CH2:3][CH2:4][CH2:5][C:6]#[C:7][CH2:8][CH2:9][CH2:10][CH3:11]>C1COCC1.[Pd]>[CH3:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][CH3:11]

Komponenten

6

Edukt 3

HCID 962Water2×HCID 160305-DecyneHCID 178527255HCID 178527255, Verbindung

Produkt 1

HCID 5364449Cis-5-DeceneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of polysiloxane containing a homogeneous dispersion of palladium particles (0.13 g) prepared as described above in THF and water (0.05 mmol Pd), 5-decyne (0.138 g, 0.18 mL, 1.0 mmol) in a solution of THF (5mL) and water (1 mL) was added. Hydrogen was bubbled through the solution for 30 seconds and the reaction was then placed under a hydrogen atmosphere (balloon). The reaction was stirred at room temperature for 4.5 h. Capillary gas chromatograph analysis showed complete consumption of the alkyne and a 94% yield of Z-5-decene using dodecane as an internal standard. The product was too volatile for an accurate isolated yield. However, a portion was isolated and analyzed spectroscopically. IR (neat) 2925.5, 2850.0 1460.1 cm -1. 1H NMR (300MHz, CDCl3)δ5.33 (br t, J=4.5 Hz, 2H), 2.01 (br q, J=5.6 Hz, 4H), 1.3-1.2 (m, 8H), 0.86 (t, J= 6.8 Hz, 6H) [>12:1 Z/E stereochemistry]. 13C NMR (20 MHz, CDCl3)δ129.87, 30.25, 26.93, 22.25, 13.98.

Aufarbeitung

  1. additionwas added
  2. customHydrogen was bubbled through the solution for 30 seconds
  3. customconsumption of the alkyne

Quellen und Nachweise

ORD-Eintrag
ord-28d070211b2e4806bfb064bc1a510d52
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05047380

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