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

HRID 1741432노트

반응식

HRID 1741432 반응식
[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

참가 물질

5

반응물 3

HCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 5360545Sodium2회HCID 21835800Ethyl 1-(p-chlorophenyl)-beta-oxocyclopropanepropionate

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매3회

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-386b673c226c4aec94b59ee7b4b8fc44
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05973190

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