반응 #2314275

반응 방정식

octylmagnesium bromide

THF

THF

→

bis-octyl ketone

수율 88.0%

반응 조건

후처리

1. 1
   기타the solution was quenched with saturated NH4Cl
2. 2
   추출was extracted with EtOAc
3. 3
   세척The combined organic layers were washed with brine
4. 4
   건조dried over MgSO4
5. 5
   기타The solvent was removed under reduced pressure
6. 6
   기타the residue was chromatographed on silica gel
7. 7
   세척Elution with 7.5% ethyl acetate in hexanes

실험 절차

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).

출처