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Hydrochloric Acid → HCID 20391996, Verbindung

HRID 1863523
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1863523
COC([C:5]1([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH:9]([CH:10]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)/[CH:11]=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:8][O:7][C:6]1=[O:25])=O.[C-]#N.[Na+].Cl>CN(C)P(=O)(N(C)C)N(C)C>[CH3:35][O:34][C:32]([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH:5]1[CH:9]([CH:10]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)/[CH:11]=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:8][O:7][C:6]1=[O:25])=[O:33]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 20391998HCID 20391998, Verbindung

Produkt 1

HCID 20391996HCID 20391996, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 12679HexamethylphosphoramideLösungsmittel

Versuchsvorschrift

1.00 g (1.98 mmol) of 3-methoxycarbonyl-3-(6-methoxycarbonylhexyl)-4-(1-phenylthio-trans-2-octenyl)-oxolane-2-one was dissolved in 23 ml of hexamethylphosphoric triamide followed by stirring. 194 mg (3.96 mmols) of sodium cyanide was then added to the solution and the mixture was heated at 75° to 80° C. for 15 hours while heating. The mixture was allowed to cool to room temperature and rendered neutral with diluted hydrochloric acid. The mixture was extracted with ethyl acetate and the extract was washed three times with water and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation and the resulting residue was purified by silica gel column chromatography using ethyl acetate and n-hexane (1:9 by volume) as an eluent to obtain 730 mg (83% yield) of 3-(6-methoxycarbonylhexyl)-4-(1-phenylthio-trans-2-octenyl)-oxolane-2-one an an oily substance.

Aufarbeitung

  1. temperaturethe mixture was heated at 75° to 80° C. for 15 hours
  2. temperaturewhile heating
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract was washed three times with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was then removed by distillation
  7. customthe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fc3509da4a024e10bf4343a62b76c22e
Quelldatensatz
uspto-grants-1979_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04169199

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