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

HRID 1607352ノート

反応式

HRID 1607352 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c426992e5f4a4f47a205ae05405fd724
出典データセット
uspto-grants-1989_09
特許番号
US04864052

反応ノート

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