Ethyl diazoacetate → Ethyl 2-(bromomethyl)-3-(3-nitrophenyl)cyclopropane Carboxylate

HRID 428913노트

반응식

HRID 428913 반응식
[Br:1][CH2:2]/[CH:3]=[CH:4]/[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1.[N+](=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N-]>ClCCl.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[Br:1][CH2:2][CH:3]1[CH:4]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=2)[CH:16]1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

참가 물질

5

반응물 2

HCID 12192Ethyl diazoacetateHCID 58409941-[(E)-3-bromo-1-propenyl]-3-nitrobenzene

생성물 1

HCID 22141287Ethyl 2-(bromomethyl)-3-(3-nitrophenyl)cyclopropane Carboxylate수율 7%

시약·촉매·용매 2

HCID 423677Acetic acid, rhodium salt (4:2)촉매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 1-[(E)-3-bromo-1-propenyl]-3-nitrobenzene (Preparation 22, 820 mg, 3.23 mmol) in dichloromethane (3 ml) was added rhodium (II) acetate dimer (20 mg, 0.046 vmnol). To the mixture was added dropwise at room temperature over 3 h a solution of ethyl diazoacetate (0.47 ml, 510 mg, 4.47 mmol) in dichloromethane (3 ml), then the mixture was stirred at room temperature for 66 h. The mixture was purified by silica (100 g) column chromatography eluting with hexane:dichloromethane 100:0 to 50:50. Product containing fractions were combined and concentrated in vacuo to afford the title compound as a colourless oil (65 mg, 7%).

후처리

  1. customThe mixture was purified by silica (100 g) column chromatography
  2. washeluting with hexane:dichloromethane 100:0 to 50:50
  3. additionProduct containing fractions
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-53b1264eeebf4f6fb441c709d4be614e
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313312B1

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