Ozone → (2-Methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-formylcyclopropanecarboxylate

HRID 1607352노트

반응식

HRID 1607352 반응식
[O:1]=[O+][O-].[CH3:4][C:5]1([CH3:29])[CH:7]([CH:8]=C(C)C)[CH:6]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17]=1[CH3:28])=[O:13]>C(OCC)(=O)C>[CH3:4][C:5]1([CH3:29])[CH:7]([CH:8]=[O:1])[CH:6]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17]=1[CH3:28])=[O:13]

참가 물질

4

반응물 2

HCID 24823OzoneHCID 13933694(2-Methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate

생성물 1

HCID 13602235(2-Methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-formylcyclopropanecarboxylate수율 92%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Ozone was bubbled at -78° C. into a solution of 698 mg (2.01 mmol) of (2-methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate obtained in Reference Example 1, in 10 ml of ethyl acetate. The supply of ozone was terminated when the solution turned slightly blue. Then, 1 ml of dimethyl sulfide was added, and the temperature of the mixture was allowed to warm to room temperature. The reaction mixture was concentrated under reduced pressure and purified by column chromatography (dichloromethane/hexane=1/1) to obtain 591 mg of (2-methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-formylcyclopropanecarboxylate.

후처리

  1. customThe supply of ozone was terminated when the solution
  2. additionThen, 1 ml of dimethyl sulfide was added
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. custompurified by column chromatography (dichloromethane/hexane=1/1)

출처 및 근거

ORD 기록
ord-c426992e5f4a4f47a205ae05405fd724
출처 데이터셋
uspto-grants-1989_09
특허 번호
US04864052

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