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

HRID 428915

Reaktionsgleichung

Reaktionsgleichung von HRID 428915
[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]

Komponenten

5

Edukt 2

HCID 12192Ethyl diazoacetateHCID 5357478Cinnamyl bromide

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 423677Acetic acid, rhodium salt (4:2)KatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c91e57f4b2e140b180b38f4cfac42ac7
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313312B1

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