Styrene → Ethyl trans-2-phenylcyclopropanecarboxylate

HRID 1485081

Reaktionsgleichung

Reaktionsgleichung von HRID 1485081
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N+](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N-]>ClCCCl.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[C:3]1([C@@H:2]2[CH2:1][C@H:11]2[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:3]1([C@H:2]2[CH2:1][C@H:11]2[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

6

Edukt 2

HCID 7501StyreneHCID 12192Ethyl diazoacetate

Produkt 2

HCID 252496Ethyl trans-2-phenylcyclopropanecarboxylateHCID 816743ethyl (1R,2S)-2-phenylcyclopropane-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 152122Dirhodium tetraacetateKatalysatorHCID 111,2-DichloroethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of styrene (3.00 g) and rhodium(II) acetate dimer (40.0 mg) in 1,2-dichloroethane (29.0 mL), a solution of ethyl diazoacetate (3.03 mL) in 1,2-dichloroethane (29.0 mL) was added over a period of 4 hours and the mixture was stirred at room temperature for 19 hours. The reaction mixture was concentrated under reduced pressure and purified by silica gel column chromatography (n-hexane:diethyl ether=20:1) to give ethyl trans-2-phenylcyclopropanecarboxylate as a colorless oil (2.42 g) and ethyl cis-2-phenylcyclopropanecarboxylate as a colorless oil (1.51 g).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by silica gel column chromatography (n-hexane:diethyl ether=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-cd51802230054e0eb6a9d8fe7618ce9e
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422240B2

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