Reaktion #2314275

Reaktionsgleichung

octylmagnesium bromide

THF

THF

→

bis-octyl ketone

Ausbeute 88.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solution was quenched with saturated NH4Cl
2. 2
   Extraktionwas extracted with EtOAc
3. 3
   WaschenThe combined organic layers were washed with brine
4. 4
   Trocknendried over MgSO4
5. 5
   SonstigeThe solvent was removed under reduced pressure
6. 6
   Sonstigethe residue was chromatographed on silica gel
7. 7
   WaschenElution with 7.5% ethyl acetate in hexanes

Vorschrift

To a solution of 4.0 g (14.5 mmol) of the LIVb in 100 mL of THF was added 20 mL (40 mmol) of 2M octylmagnesium bromide in THF dropwise. After stiring 3.5 h, the solution was quenched with saturated NH4Cl, acidified with 1N HCl, and was extracted with EtOAc. The combined organic layers were washed with brine and dried over MgSO4. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel. Elution with 7.5% ethyl acetate in hexanes gave 4.86 g (88%) of the bis-octyl ketone LIVc as an oil. 1H NMR (300 MHz, CDCl3) δ 4.55 (s, 2H, CH), 2.64 (dt, 4H, CH2), 1.62 (m, 4H, CH2), 1.42 (s, 6H, CH3), 1.27 (broad s, 20H, CH2), 0.88 (t, 6H, CH3); MS (CI,NH3) m/e 383 (M+1).

Quelle