Cyclopropanecarbonyl chloride → Ethyl 4-cyclopropyl-4-oxobutanoate

HRID 1046063Notes

Reaction equation

HRID 1046063 reaction equation
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

Participants

8

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 10911297Ethyl 3-iodopropanoate

Product 1

HCID 24727441Ethyl 4-cyclopropyl-4-oxobutanoateYield 70.5%

Reagents, catalysts & solvents 5

HCID 10290809Zinc copper coupleCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 241BenzeneSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-7fcecf852594480a9984f12e2cad41b5
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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