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

HRID 907661

反応式

HRID 907661 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 702Ethanol溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-bcf0b64428bd46c1b274d440febbb1c9
出典データセット
uspto-grants-2011_09
特許番号
US08013166B2

関連ノート

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