diazo-(3,4-Difluoro-phenyl)acetic acid allyl ester → 1-(3,4-Difluoro-phenyl)-3-oxa-bicyclo[3.1.0]hexan-2-one

HRID 1172216ノート

反応式

HRID 1172216 の反応式
[CH2:1]([O:4][C:5](=[O:17])[C:6](=[N+]=[N-])[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([F:14])[CH:8]=1)[CH:2]=[CH2:3]>ClCCl.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCC(O)=O.[Rh].[Rh]>[F:14][C:9]1[CH:8]=[C:7]([C:6]23[CH2:3][CH:2]2[CH2:1][O:4][C:5]3=[O:17])[CH:12]=[CH:11][C:10]=1[F:13]

参加物

4

反応物 1

HCID 86609586diazo-(3,4-Difluoro-phenyl)acetic acid allyl ester

生成物 1

HCID 674239031-(3,4-Difluoro-phenyl)-3-oxa-bicyclo[3.1.0]hexan-2-one収率 72.9%

試薬・触媒・溶媒 2

HCID 6099591Rhodium(II) Octanoate Dimer触媒HCID 6344Dichloromethane溶媒2 回

実験手順

Diazo-(3,4-Difluoro-phenyl)acetic acid allyl ester (70 g) was dissolved in dichloromethane (1000 mL) and added slowly during 36 h via a syringe pump (alternatively it is added dropwise via an addition funnel; 30 mL pr. hour) to a refluxing solution of rhodium (II) octanoate dimer (1.17 g, 1.5 mmol) in dichloromethane (200 mL). After all diazo compound has been added, the mixture is refluxed for another 30 min, then was evaporated in vacuo and crystallised by addition of cyclohexane (200 mL). This gave 30 g crystalline. Further 15 g was isolated from the motherliq. by repeated evaporation and crystallisation giving in total 45 g 1-(3,4-Difluoro-phenyl)-3-oxa-bicyclo[3.1.0]hexan-2-one.

後処理

  1. additionadded slowly during 36 h via a syringe pump (alternatively it
  2. additionis added dropwise via an addition funnel
  3. temperaturethe mixture is refluxed for another 30 min
  4. customwas evaporated in vacuo
  5. customcrystallised by addition of cyclohexane (200 mL)
  6. customFurther 15 g was isolated from the motherliq
  7. customevaporation and crystallisation

出典と根拠

ORDレコード
ord-5e719263b8b04264999ad1310e29f7d1
出典データセット
uspto-grants-2010_11
特許番号
US07834008B2

反応ノート

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