반응 #59153

반응 방정식

Ethyl acetate

diethyl 2-phenylethylmalonate

sodium hydride

2-bromo-1-(3-methyl-4′-nitro-1,1′-biphenyl-4-yl)ethanone

→

diethyl 2-[2-(3-methyl-4′-nitro-1,1′-biphenyl-4yl)-2-oxoethyl]-2-(2-phenylethyl)malonate

수율 85.3%

용매

water

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   기타The ice bath was removed
2. 2
   workup.STIRRINGthe resulting mixture was stirred at rt for about 70 h
3. 3
   기타the layers were separated
4. 4
   세척The organic layer was washed with water (2×30 mL)
5. 5
   건조dried over magnesium sulfate
6. 6
   농축concentrated under reduced pressure
7. 7
   기타to give a dark, brown oil
8. 8
   기타This material was purified by flash chromatography (10:90 ethyl acetate/hexane)

실험 절차

To a cold suspension (0-5° C.) of 95% sodium hydride (3.53 g, 13.0 mmol) in dry tetrahydrofuran (30 mL) was slowly added diethyl 2-phenylethylmalonate (3.53 g, 13 mmol). The ice bath was removed and the reaction mixture was stirred at rt for 45 minutes. A solution of 2-bromo-1-(3-methyl-4′-nitro-1,1′-biphenyl-4-yl)ethanone (4.06 g, 12.0 mmol) in dry tetrahydrofuran (50 mL) was slowly added, and the resulting mixture was stirred at rt for about 70 h. Ethyl acetate (80 mL) and water (20 mL) were added, and the layers were separated. The organic layer was washed with water (2×30 mL), dried over magnesium sulfate, and concentrated under reduced pressure to give a dark, brown oil. This material was purified by flash chromatography (10:90 ethyl acetate/hexane) to give diethyl 2-[2-(3-methyl-4′-nitro-1,1′-biphenyl-4yl)-2-oxoethyl]-2-(2-phenylethyl)malonate as a light yellow oil (5.30 g, 82% yield). LC-MS ret. time 4.01 min, m/z 517.9 (MH+); 1H NMR (CDCl3) δ 1.23-1.35 (m, 6H), 2.41-2.50 (m, 2H), 2.56 (s, 3H), 2.59-2.66 (m, 2H), 3.71 (s, 2H), 4.21-4.32 (m, 4H), 7.13-7.19 (m, 3H), 7.22-7.30 (m, 2H), 7.49-7.55 (m, 2H), 7.73-7.82 (m, 3H), 8.31 (d, 2H).

출처