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Nitromethane → HCID 131728908, Verbindung

HRID 551658
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 551658
[CH:1]1([C:6]2[CH2:7][C@@H:8]3[C@H:11]([CH:12]=2)[C:10](=[CH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]3)[CH2:5][CH2:4][CH2:3][CH2:2]1.N12CCCN=C1CCCCC2.P([O-])(O)(O)=O.[K+].[N+:38]([CH3:41])([O-:40])=[O:39]>>[N+:38]([CH2:41][C@@:10]1([CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][C@H:8]2[C@@H:11]1[CH:12]=[C:6]([CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH2:7]2)([O-:40])=[O:39]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 6375NitromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516951Monobasic potassium phosphateHCID 131728907HCID 131728907, Verbindung

Produkt 1

HCID 131728908HCID 131728908, Verbindung

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Tert-butyl(±)-[(1S,5R)-3-cyclopentylbicyclo[3.2.0]hept-3-en-6-ylidene]acetate (3.30 g, 12.0 mmol) was dissolved in nitromethane (30 mL). To the solution, 1,8-diazabicyclo[5.4.0]undec-7-ene (2.20 g, 14.5 mmol) was added, and the mixture was stirred at 60° C. for 5 hours. The mixture was allowed to cool, and a saturated aqueous solution of potassium dihydrogen phosphate was then added thereto, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography to obtain the compound of interest as a yellow oil substance (3.50 g, 87%).

Aufarbeitung

  1. temperatureto cool
  2. extractionfollowed by extraction with dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel chromatography
  6. customto obtain the compound of interest as a yellow oil substance (3.50 g, 87%)

Quellen und Nachweise

ORD-Eintrag
ord-f263541449854ea0bb1741cad83bba81
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07947738B2

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