1-(Bromomethyl)-3-phenoxybenzene → Ethyl 1-(p-chlorophenyl)-beta-oxo-alpha-(m-phenoxybenzyl)cyclopropanepropionate

HRID 1741432ノート

反応式

HRID 1741432 の反応式
[Na].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:12](=[O:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[C:20]1([O:26][C:27]2[CH:28]=[C:29]([CH2:33]Br)[CH:30]=[CH:31][CH:32]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2([C:12](=[O:19])[CH:13]([CH2:33][C:29]3[CH:30]=[CH:31][CH:32]=[C:27]([O:26][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:28]=3)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 5360545Sodium2 回HCID 21835800Ethyl 1-(p-chlorophenyl)-beta-oxocyclopropanepropionate

生成物 1

HCID 11070385Ethyl 1-(p-chlorophenyl)-beta-oxo-alpha-(m-phenoxybenzyl)cyclopropanepropionate収率 92%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒3 回

反応条件

温度
70 °C

実験手順

A mixture of sodium (0.31 g, 13.5 mmol) in ethanol (90 mL) is stirred at room temperature until the sodium dissolves. The resultant solution is heated to 70° C., treated dropwise with a solution of ethyl 1-(p-chlorophenyl)-β-oxocyclopropanepropionate (3.4 g, 12.8 mmol) in ethanol, stirred at 70° C. for one hour, treated dropwise with a solution of α-bromo-m-tolyl phenyl ether (4.0 g, 15.2 mmol) in ethanol, stirred at reflux overnight, stirred at room temperature for two days, and concentrated in vacuo to obtain a residue. A solution of the residue in ethyl acetate is washed sequentially with water, 10% sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain an oil. Chromatography of the oil using silica gel and a 19:1 hexanes/ethyl acetate solution gives the title product as a colorless oil (5.24 g, 92%) which is identified by NMR spectral analysis.

後処理

  1. dissolutiondissolves
  2. stirringstirred
  3. temperatureat reflux overnight
  4. stirringstirred at room temperature for two days
  5. concentrationconcentrated in vacuo
  6. customto obtain a residue
  7. washA solution of the residue in ethyl acetate is washed sequentially with water, 10% sodium hydrogen carbonate solution and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customto obtain an oil

出典と根拠

ORDレコード
ord-386b673c226c4aec94b59ee7b4b8fc44
出典データセット
uspto-grants-1999_10
特許番号
US05973190

反応ノート

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