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

HRID 1826417ノート

反応式

HRID 1826417 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 423677Acetic acid, rhodium salt (4:2)触媒HCID 6344Dichloromethane溶媒2 回

実験手順

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 mmol). 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%).

後処理

  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

出典と根拠

ORDレコード
ord-2c956626e6e0440e8bc251c0b37d233b
出典データセット
uspto-grants-2006_05
特許番号
US07049444B2

反応ノート

読み込み中…