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Toluene → 1-Benzyl-4-[3-(ethoxycarbonyl)-1-fluorocyclobutan-3-yl]-2-pyrrolidone

HRID 1279665
ノート
印刷プレビュー

反応式

HRID 1279665 の反応式
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16][CH:15](O)[CH2:14]2)[CH2:10][C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.C(N(S(F)(F)[F:37])CC)C.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.ClCCl>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16][CH:15]([F:37])[CH2:14]2)[CH2:10][C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 1140TolueneHCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 184277971-Benzyl-4-[3-(ethoxycarbonyl)-1-hydroxycyclobutan-3-yl]-2-pyrrolidone

生成物 1

HCID 184278031-Benzyl-4-[3-(ethoxycarbonyl)-1-fluorocyclobutan-3-yl]-2-pyrrolidone収率 80%

試薬・触媒・溶媒 2

HCID 6212
Chloroform
溶媒
HCID 6344Dichloromethane溶媒

実験手順

A 495 mg (1.56 mmol) portion of 1-benzyl-4-[3-(ethoxycarbonyl)-1-hydroxycyclobutan-3-yl]-2-pyrrolidone (Isomer A) was dissolved in a mixed solvent consisting of 12 ml of toluene and 6 ml of dichloromethane to which, while cooling in an ice bath with stirring, was then added 839 μl (6.24 mmol) of diethylaminosulfur trifluoride, subsequently carrying out 20 hours of stirring at 40° C. While cooling in an ice bath with stirring, the reaction solution was alkalified by slowly adding saturated sodium bicarbonate aqueous solution and then mixed with chloroform to carry out separation of layers, and the resulting organic layer was washed with saturated brine. The aqueous layer was again extracted with chloroform, and the organic layers were combined and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under a reduced pressure and the resulting residue was purified by a silica gel column chromatography (n-hexane:ethyl acetate=2:1) to give 400 mg (80.0%) of the title compound.

後処理

  1. temperaturewhile cooling in an ice bath
  2. stirringof stirring at 40° C
  3. temperatureWhile cooling in an ice bath
  4. stirringwith stirring
  5. customseparation of layers
  6. washthe resulting organic layer was washed with saturated brine
  7. extractionThe aqueous layer was again extracted with chloroform
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationAfter filtration
  10. customthe solvent was evaporated under a reduced pressure
  11. customthe resulting residue was purified by a silica gel column chromatography (n-hexane:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-665a847fd75545f88914db7b2057520f
出典データセット
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06448266B1

反応ノート

読み込み中…

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