Ethyl diazoacetate → Cyclopropanecarboxylic acid, 2-(3-methoxyphenyl)-, ethyl ester

HRID 1994101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1994101
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]=[CH2:10])[CH:4]=1.[N+](=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N-]>C(Cl)Cl.O=C=O.C([Rh]CCCCCCC)CCCCCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:10][CH:13]2[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 2

HCID 12192Ethyl diazoacetateHCID 5841461-Ethenyl-3-methoxybenzene

Produkt 1

HCID 19358490Cyclopropanecarboxylic acid, 2-(3-methoxyphenyl)-, ethyl esterAusbeute 63,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178443918HCID 178443918, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture of 1-methoxy-3-vinylbenzene (3.10 g, 23.1 mmol) and dioxomethane-diheptylrhodium (4:2) (0.090 g, 0.12 mmol) in DCM (100 mL) under an atmosphere of argon at rt was added a solution of ethyl diazoacetate (1.22 mL, 11.6 mmol) in DCM (6 mL) dropwise via syringe. The reaction mixture as allowed to stir at rt for 2 h and then concentrated. The residue was purified by column chromatography to give the desired product (1.63 g) as a mixture of cis and trans isomers, along with recovered starting material (1.50 g). LCMS: (FA) ES+ 221.2 (M+1).

Aufarbeitung

  1. concentrationconcentrated
  2. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e147f22341264f398d82f9e4c4f48611
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652041B2

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