Cyclopropanecarbonyl chloride → Ethyl 4-cyclopropyl-4-oxobutanoate

HRID 1046063노트

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HRID 1046063 반응식
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

참가 물질

8

반응물 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 10911297Ethyl 3-iodopropanoate

생성물 1

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

시약·촉매·용매 5

HCID 10290809Zinc copper couple촉매HCID 178418476HCID 178418476, 화합물촉매HCID 241Benzene용매HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

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온도
60 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-7fcecf852594480a9984f12e2cad41b5
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569292B2

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