تفاعل #2314275

معادلة التفاعل

octylmagnesium bromide

THF

THF

→

bis-octyl ketone

المردود 88.0%

ظروف التفاعل

المعالجة

1. 1
   أخرىthe solution was quenched with saturated NH4Cl
2. 2
   استخلاصwas extracted with EtOAc
3. 3
   غسيلThe combined organic layers were washed with brine
4. 4
   تجفيفdried over MgSO4
5. 5
   أخرىThe solvent was removed under reduced pressure
6. 6
   أخرىthe residue was chromatographed on silica gel
7. 7
   غسيلElution with 7.5% ethyl acetate in hexanes

الإجراء التجريبي

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).

المصدر