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

HRID 30841ノート

反応式

HRID 30841 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 702Ethanol溶媒

反応条件

温度
55 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d7b56ec60c7b450b8d08be05331113a6
出典データセット
uspto-grants-2008_09
特許番号
US07423156B2

反応ノート

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