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

HRID 428915

반응식

HRID 428915 반응식
[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]

참가 물질

5

반응물 2

HCID 12192Ethyl diazoacetateHCID 5357478Cinnamyl bromide

생성물 1

HCID 22141265Ethyl 2-(bromomethyl)-3-phenylcyclopropanecarboxylate수율 8%

시약·촉매·용매 2

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

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-c91e57f4b2e140b180b38f4cfac42ac7
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313312B1

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