Sodium Hydroxide → Ethyl 4-(4-bromophenyl)-4-oxo-2-(2-phenylethyl)butanoate

HRID 9524

반응식

HRID 9524 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:29])[CH2:9][C:10]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(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:3]=[CH:4][C:5]([C:8](=[O:29])[CH2:9][CH:10]([CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 21985802Diethyl 2-[2-(4-bromophenyl)-2-oxoethyl]-2-(2-phenylethyl)malonate

생성물 1

HCID 21985805Ethyl 4-(4-bromophenyl)-4-oxo-2-(2-phenylethyl)butanoate수율 65%

시약·촉매·용매 2

HCID 180Acetone용매HCID 702Ethanol용매

반응 조건

온도
50 °C

실험 절차

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).

후처리

  1. customSolvent was then removed under reduced pressure via rotary evaporation
  2. concentrationthe resulting residue was further concentrated under high vacuum for 1 h
  3. dissolutionThe residue was redissolved in dimethoxyethane (18.5 mL)
  4. temperaturethe solution was heated at 80° C. for 2.5 h
  5. temperatureThe mixture was cooled to rt
  6. additiondiluted with ethyl acetate
  7. washwashed with water
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. concentrationconcentrated under high vacuum
  10. customThe resulting residue was purified by flash chromatography (Biotage flash 75, 10:90 ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-8fb6d4a6537a45d7bc04373d65cf36ce
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091228B2

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