Sodium → 3-[(2-Nitroethyl)sulfanyl]cyclohept-1-ene

HRID 46739

Reaktionsgleichung

Reaktionsgleichung von HRID 46739
[Na].[C:2]([S:5][CH:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=[CH:7]1)(=O)[CH3:3].[N+:13](CCOC(=O)C)([O-:15])=[O:14]>C(O)C>[N+:13]([CH2:3][CH2:2][S:5][CH:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=[CH:7]1)([O-:15])=[O:14]

Komponenten

5

Edukt 3

HCID 5360545SodiumHCID 118153992-nitroethyl AcetateHCID 126209593-Acetylmercaptocycloheptene

Produkt 1

HCID 126210093-[(2-Nitroethyl)sulfanyl]cyclohept-1-eneAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel3×

Versuchsvorschrift

To 40 ml of absolute ethanol was added 1.38 g (0.060 gram atom) metallic sodium. When the reaction was completed, 10.2 g (0.060 mole) of 3-acetylmercaptocycloheptene in 20 ml of absolute ethanol was added and the reaction mixture was brought up to reflux for 15 minutes. The solution was then cooled to 0° and 7.98 g (0.060 mole) of 1-nitro-2-acetoxyethane in 20 ml absolute ethanol was added. The reaction was allowed to proceed for 3.0 hours at 0° and then was partitioned between 1 N HCl and methylene chloride. The aqueous phase was further extracted with methylene chloride. The organic phases were pooled, dried over sodium sulfate, and evaporated to afford 12 g (99%) of pure 3-[2-nitroethylthio]cycloheptene as a colorless oil.

Aufarbeitung

  1. temperatureto reflux for 15 minutes
  2. temperatureThe solution was then cooled to 0°
  3. customwas partitioned between 1 N HCl and methylene chloride
  4. extractionThe aqueous phase was further extracted with methylene chloride
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a8fed77ef40e48b4850d99848d9e4d07
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04175086

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