Reaktion #65583

Reaktionsgleichung

cyclododecane carboxaldehyde

phenylethyl triphenylphosphonium bromide

butyllithium

→

colorless oil

Ausbeute 88.2%

1-(3-phenyl-1-propenyl)cyclododecane

Ausbeute 88.2%

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture is stirred at room temperature for 3 hours after which time no starting material
2. 2
   SonstigeThe reaction mixture is quenched with 1N HCl
3. 3
   SonstigeThe layers are separated
4. 4
   Waschenthe aqueous layer is washed twice with ethyl ether
5. 5
   TrocknenThe combined organic layers are dried over a MgSO4
6. 6
   Sonstigethe ether is evaporated
7. 7
   Sonstigechromatographed on silica gel

Vorschrift

To 11.4 g (25.5 mmol) of phenylethyl triphenylphosphonium bromide in 50 mL of dry ether at 0° C. is added 10.2 mL (25.5 mmol) of 2.5M butyllithium. The suspension is stirred at 0° C. for 1 hour followed by the addition of 5.0 g (25.5 mmol) of cyclododecane carboxaldehyde. The mixture is stirred at room temperature for 3 hours after which time no starting material is evident by TLC. The reaction mixture is quenched with 1N HCl. The layers are separated and the aqueous layer is washed twice with ethyl ether. The combined organic layers are dried over a MgSO4 and the ether is evaporated. The residue is flash chromatographed on silica gel using hexanes to give 6.4 g of a colorless oil: NMR (CDCl3) δ 1.0-1.6 (m, 10H), 2.6 (m, 1H), 3.4 (d, 2H, J=8 Hz, ), 5.3 (t, 1H, J=7 Hz), 5.45 (q, 1H, J=7 Hz), 7.2 ppm (m, 5H).

Quelle