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Dimethyl Sulfoxide → 1-Cyclopropanecarbonylpiperidin-4-one

HRID 129502
ノート
印刷プレビュー

反応式

HRID 129502 の反応式
[C:1](Cl)(=[O:5])[C:2](Cl)=O.CS(C)=[O:9].[CH2:11]([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])C.Cl[CH:19](Cl)[CH3:20]>ClCCl>[CH:15]1([C:14]([N:13]2[CH2:11][CH2:2][C:1](=[O:5])[CH2:17][CH2:16]2)=[O:9])[CH2:20][CH2:19]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 63651,1-DichloroethaneHCID 8471TriethylamineHCID 65578Oxalyl chloride

生成物 1

HCID 149949681-Cyclopropanecarbonylpiperidin-4-one収率 76%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

66 g of oxalic chloride was dissolved in 500 ml of dichloroethane, into which 61 g of dimethyl sulfoxide was gradually dropped at -67° C. 44 g of 1-cycloprpanecarbonyl-4-hydroxypiperidine dissolved in 200 ml of dichloromethane was dropped into the above solution at -67° C. At -67° C., 131 g of triethylamine was further added, followed by returning to room temperature. The resultant salt was removed by filtration and the filtrate was once concentrated, after which water was added to the concentrate, followed by extraction with ethyl acetate and drying with anhydrous magnesium sulfate. Moreover, the aqueous phase was extracted with chloroform and dried similarly. The solvent was distilled off under reduced pressure and the resultant reside was purified by the use of silica gel column chromatography (elution solvent: ethyl acetate:hexane=3:7), thereby obtaining 33 g of the intended compound (yield 76%).

後処理

  1. additionwas gradually dropped at -67° C
  2. additionwas dropped into the above solution at -67° C
  3. customby returning to room temperature
  4. customThe resultant salt was removed by filtration
  5. concentrationthe filtrate was once concentrated
  6. additionafter which water was added to the concentrate
  7. extractionfollowed by extraction with ethyl acetate
  8. dry with materialdrying with anhydrous magnesium sulfate
  9. extractionMoreover, the aqueous phase was extracted with chloroform
  10. customdried similarly
  11. distillationThe solvent was distilled off under reduced pressure
  12. customthe resultant reside was purified by the use of silica gel column chromatography (elution solvent: ethyl acetate:hexane=3:7)

出典と根拠

ORDレコード
ord-ed99b4b9ee0346ff84d4dcd6928e88df
出典データセット
uspto-grants-1995_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05468740

反応ノート

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