Reacción #2314275

Ecuación de reacción

octylmagnesium bromide

THF

THF

→

bis-octyl ketone

Rendimiento 88.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solution was quenched with saturated NH4Cl
2. 2
   Extracciónwas extracted with EtOAc
3. 3
   LavadoThe combined organic layers were washed with brine
4. 4
   Secadodried over MgSO4
5. 5
   OtroThe solvent was removed under reduced pressure
6. 6
   Otrothe residue was chromatographed on silica gel
7. 7
   LavadoElution with 7.5% ethyl acetate in hexanes

Procedimiento

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).

Fuente