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

반응식

HRID 1172216 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 6099591Rhodium(II) Octanoate Dimer촉매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5e719263b8b04264999ad1310e29f7d1
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834008B2

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