Ethyl diazoacetate → Ethyl 2-(bromomethyl)-3-phenylcyclopropanecarboxylate

HRID 428915ノート

反応式

HRID 428915 の反応式
[Br:1][CH2:2]/[CH:3]=[CH:4]/[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N+](=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[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]=[CH:7][CH:6]=2)[CH:13]1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

参加物

5

反応物 2

HCID 12192Ethyl diazoacetateHCID 5357478Cinnamyl bromide

生成物 1

HCID 22141265Ethyl 2-(bromomethyl)-3-phenylcyclopropanecarboxylate収率 8%

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 [(E)-3-bromo-1-propenyl]benzene (705 mg, 3.58 mmol) in dichloromethane (1 ml) was added rhodium (II) acetate dimer (20 mg, 0.05 mmol). To the mixture was added dropwise at room temperature over 4 h a solution of ethyl diazoacetate (0.43 ml, 0.47 g, 4.15 mmol) in dichloromethane (2.5 ml). The mixture was stirred at room temperature for 60 h. The mixture was purified by silica column (40 g) chromatography eluting with 1:1 hexane:dichloromethane then dichloromethane. Product-containing fractions were purified further by silica column (10 g) chromatography eluting with 9:1 hexane:dichloromethane then dichloromethane. Product-containing fractions were combined and concentrated in vacuo to give the title compound as a colourless oil (75 mg, 8%).

後処理

  1. customThe mixture was purified by silica column (40 g) chromatography
  2. washeluting with 1:1 hexane
  3. customProduct-containing fractions were purified further by silica column (10 g) chromatography
  4. washeluting with 9:1 hexane
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-c91e57f4b2e140b180b38f4cfac42ac7
出典データセット
uspto-grants-2001_11
特許番号
US06313312B1

反応ノート

読み込み中…