تفاعل #9620

معادلة التفاعل

diethyl 2-[2-(4-bromophenyl)-2-oxoethyl]-2-(2-phenylethyl)malonate

sodium hydroxide

→

ethyl 4-(4-bromophenyl)-4-oxo-2-(2-phenylethyl)butanoate

المردود 65.0%

المذيبات

acetone

ethanol

ظروف التفاعل

المعالجة

1. 1
   أخرىSolvent was then removed under reduced pressure via rotary evaporation
2. 2
   تركيزthe resulting residue was further concentrated under high vacuum for 1 h
3. 3
   workup.DISSOLUTIONThe residue was redissolved in dimethoxyethane (18.5 mL)
4. 4
   درجة الحرارةthe solution was heated at 80° C. for 2.5 h
5. 5
   درجة الحرارةThe mixture was cooled to rt
6. 6
   workup.ADDITIONdiluted with ethyl acetate
7. 7
   غسيلwashed with water
8. 8
   تجفيفThe organic layer was dried over anhydrous sodium sulfate
9. 9
   تركيزconcentrated under high vacuum
10. 10
    أخرىThe resulting residue was purified by flash chromatography (Biotage flash 75, 10:90 ethyl acetate/hexane)

الإجراء التجريبي

To a solution of diethyl 2-[2-(4-bromophenyl)-2-oxoethyl]-2-(2-phenylethyl)malonate (7.89 g, 17.1 mmol) in acetone (18.5 mL) and ethanol (17.0 mL) was added 1 N aqueous sodium hydroxide solution (17.1 mL), and the resulting solution was heated at 50° C. for 3 h. Solvent was then removed under reduced pressure via rotary evaporation and the resulting residue was further concentrated under high vacuum for 1 h. The residue was redissolved in dimethoxyethane (18.5 mL) and the solution was heated at 80° C. for 2.5 h. The mixture was cooled to rt, diluted with ethyl acetate, and washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated under high vacuum. The resulting residue was purified by flash chromatography (Biotage flash 75, 10:90 ethyl acetate/hexane) to afford ethyl 4-(4-bromophenyl)-4-oxo-2-(2-phenylethyl)butanoate (4.32 g, 65%). LC-MS ret. time 3.79 min, m/z 389.2 (MH+); 1H NMR (300 MHz, CDCl3) δ 1.20 (t, 3H), 1.78–1.94 (m, 2H), 2.62 (t, 2H), 2.86–3.01 (m, 2H), 3.26–3.36 (m, 1H), 4.10 (q, 2H), 7.05–7.11 (m, 3H), 7.18–7.23 (m, 2H), 7.51 (d, 2H), 7.72 (d, 2H).

المصدر