Cyclopropanecarbonyl chloride → Ethyl 4-cyclopropyl-4-oxobutanoate

HRID 1046063ノート

反応式

HRID 1046063 の反応式
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

参加物

8

反応物 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 10911297Ethyl 3-iodopropanoate

生成物 1

HCID 24727441Ethyl 4-cyclopropyl-4-oxobutanoate収率 70.5%

試薬・触媒・溶媒 5

HCID 10290809Zinc copper couple触媒HCID 178418476HCID 178418476、化合物触媒HCID 241Benzene溶媒HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-7fcecf852594480a9984f12e2cad41b5
出典データセット
uspto-grants-2013_10
特許番号
US08569292B2

反応ノート

読み込み中…