Water → 2,2-Dimethyl-3-(2-ethyl-2-phenyl-vinyl)cyclopropanecarboxylic acid ethyl ester

HRID 1980206노트

반응식

HRID 1980206 반응식
C(OP([CH:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:10][CH3:11])(=O)OCC)C.[CH2:18]([O:20][C:21]([C@H:23]1[C@H:25]([CH:26]=O)[C:24]1([CH3:29])[CH3:28])=[O:22])[CH3:19].O>O1CCCC1>[CH2:18]([O:20][C:21]([CH:23]1[CH:25]([CH:26]=[C:9]([CH2:10][CH3:11])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:24]1([CH3:28])[CH3:29])=[O:22])[CH3:19]

참가 물질

5

반응물 3

HCID 962WaterHCID 152542301-Diethoxyphosphoryl-propyl-benzeneHCID 86738534trans-2,2-Dimethyl-3-formyl-cyclopropanecarboxylic acid ethyl ester

생성물 1

HCID 541792012,2-Dimethyl-3-(2-ethyl-2-phenyl-vinyl)cyclopropanecarboxylic acid ethyl ester수율 52%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

51.2 g (0.2 mol) of 1-phenylpropyl-phosphonic acid diethyl ester, dissolved in 30 ml of anhydrous tetrahydrofuran, were added dropwise to a mixture of 24 g (0.214 mol) of potassium tert.-butylate and 300 ml of anhydrous tetrahydrofuran at 20°-25° C., while stirring. After the mixture had been subsequently stirred at 20°-25° C. for a further 2 hours, 34 g (0.2 mol) of cis/trans-2,2-dimethyl-3-formyl-cyclopropanecarboxylic acid ethyl ester, dissolved in 50 ml of anhydrous tetrahydrofuran, were added dropwise at 25° C., while stirring. Stirring was then continued at 60° C. for a further 6 hours. 500 ml of water were then added and the reaction mixture was extracted twice with 300 ml of methylene chloride each time. The organic phases were separated off and dried over magnesium sulphate, the solvent was distilled off under a waterpump vacuum and the residue was distilled in vacuo. 28.3 g (52% of theory) of 2,2-dimethyl-3-(2-ethyl-2-phenyl-vinyl)cyclopropanecarboxylic acid ethyl ester (isomer mixture) were obtained as a yellow oil with a boiling point of 142°-150° C./2 mbar.

후처리

  1. stirringAfter the mixture had been subsequently stirred at 20°-25° C. for a further 2 hours
  2. additionwere added dropwise at 25° C.
  3. stirringwhile stirring
  4. stirringStirring
  5. extractionthe reaction mixture was extracted twice with 300 ml of methylene chloride each time
  6. customThe organic phases were separated off
  7. dry with materialdried over magnesium sulphate
  8. distillationthe solvent was distilled off under a waterpump vacuum
  9. distillationthe residue was distilled in vacuo

출처 및 근거

ORD 기록
ord-79fa6a0e9a0145c192cab0a3a5a0754b
출처 데이터셋
uspto-grants-1984_11
특허 번호
US04485252

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