Sodium Hydroxide → Ethyl 4-(4-bromophenyl)-2-(2-methoxyethyl)-4-oxobutanoate

HRID 9529

반응식

HRID 9529 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:25])[CH2:9][C:10]([CH2:21][CH2:22][O:23][CH3:24])(C(OCC)=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1.[OH-].[Na+]>CC(C)=O.C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:25])[CH2:9][CH:10]([CH2:21][CH2:22][O:23][CH3:24])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 21985752Diethyl 2-[2-(4-bromophenyl)-2-oxoethyl]-2-(2-methoxyethyl)malonate

생성물 1

HCID 21985699Ethyl 4-(4-bromophenyl)-2-(2-methoxyethyl)-4-oxobutanoate수율 86%

시약·촉매·용매 2

HCID 180Acetone용매HCID 702Ethanol용매

반응 조건

온도
55 °C

실험 절차

To a 150 mL flask was added diethyl 2-[2-(4-bromophenyl)-2-oxoethyl]-2-(2-methoxyethyl)malonate (1.59 g, 3.59 mmol) dissolved in acetone (16 mL) and ethanol (16 mL), followed by addition of 1N aqueous sodium hydroxide solution (3.6 mL). The reaction mixture was then heated at 55° C. for 3 h. The reaction mixture was concentrated in vacuo to remove solvents, the residue redissolved in dimethoxyethane (32 mL), and the reaction mixture heated at 80° C. for 3 h. The reaction mixture was cooled to rt, diluted with ethyl acetate (50 mL) and water (50 mL), and stirred for 15 minutes until almost all color was extracted into the organic layer. The layers were separated, the aqueous layer was extracted with additional ethyl acetate (50 mL), and the combined organic layers were washed with saturated aqueous sodium chloride solution (50 mL), dried over anhydrous sodium sulfate, and concentrated in vacuo, to afford ethyl 4-(4-bromophenyl)-2-(2-methoxyethyl)-4-oxobutanoate (1.06 g, 86%). No further purification of this material was required. LC-MS ret. time 3.18 min, m/z 342.8 (MH+); 1H NMR (300 MHz, CDCl3) δ 1.35 (t, 3H), 1.77–1.92 (m, 1H), 1.94–2.10 (m, 1H), 3.05–3.2 (m, 2H), 3.35–3.50 (m, 3H), 4.09–4.25 (m, 2H), 7.60 (d, 2H), 7.83 (d, 2H).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto remove solvents
  3. dissolutionthe residue redissolved in dimethoxyethane (32 mL)
  4. temperaturethe reaction mixture heated at 80° C. for 3 h
  5. temperatureThe reaction mixture was cooled to rt
  6. additiondiluted with ethyl acetate (50 mL) and water (50 mL)
  7. extractionwas extracted into the organic layer
  8. customThe layers were separated
  9. extractionthe aqueous layer was extracted with additional ethyl acetate (50 mL)
  10. washthe combined organic layers were washed with saturated aqueous sodium chloride solution (50 mL)
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4d6fa58708e84e73b1226055e2995034
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091228B2

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