反应详情

To a solution of the product of Example 1 (4.0 g, 14.5 mmol) in THF (100 mL) was added a solution of 2M octylmagnesium bromide in THF (20 mL, 40 mmol) dropwise. After stirring for 3.5 hr, 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 the bis-octyl ketone (III) (4.86 g, 88%) 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)

1. customthe solution was quenched with saturated NH4Cl
2. extractionwas extracted with EtOAc
3. washThe combined organic layers were washed with brine
4. dry with materialdried over MgSO4
5. customThe solvent was removed under reduced pressure
6. customthe residue was chromatographed on silica gel
7. washElution with 7.5% ethyl acetate in hexanes