反応 #2314275

反応方程式

octylmagnesium bromide

THF

THF

→

bis-octyl ketone

収率 88.0%

反応条件

後処理

1. 1
   その他the solution was quenched with saturated NH4Cl
2. 2
   抽出was extracted with EtOAc
3. 3
   洗浄The combined organic layers were washed with brine
4. 4
   乾燥dried over MgSO4
5. 5
   その他The solvent was removed under reduced pressure
6. 6
   その他the residue was chromatographed on silica gel
7. 7
   洗浄Elution with 7.5% ethyl acetate in hexanes

実験手順

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).

出典