Cyclopropanecarbonyl chloride → Ethyl 4-cyclopropyl-4-oxobutanoate

HRID 1046063Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1046063
I[CH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH:9]1([C:12](Cl)=[O:13])[CH2:11][CH2:10]1>C1C=CC=CC=1.CC(N(C)C)=O.C(OCC)(=O)C.[Cu].[Zn].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:9]1([C:12](=[O:13])[CH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:11][CH2:10]1

Komponenten

8

Edukt 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 10911297Ethyl 3-iodopropanoate

Produkt 1

HCID 24727441Ethyl 4-cyclopropyl-4-oxobutanoateAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 10290809Zinc copper coupleKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 241BenzeneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of ethyl 3-iodopropanoate (8 g, 35 mmol) and zinc-copper (4.5 g, 70 mmol) in a mixture of benzene (80 mL) and DMA (8 mL) was heated at 60° C. for 4.5 hours under N2. Pd(PPh3)2Cl2 (1.2 g, 1.8 mmol) was added, followed by addition of cyclopropanecarbonyl chloride (3.7 g, 35 mmol). The mixture was stirred at 60° C. for another 30 minutes. The reaction mixture was diluted with ethyl acetate (300 mL), and washed with 1N HCl (50 mL), satd aq NaHCO3 (80 mL) and brine (30 mL). The organic layer was dried over Na2SO4 and concentrated to afford the ethyl 4-cyclopropyl-4-oxobutanoate (4.2 g), which was used for next step directly without purification.

Aufarbeitung

  1. washwashed with 1N HCl (50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7fcecf852594480a9984f12e2cad41b5
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569292B2

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