Reaktion #990808

Reaktionsgleichung

1-nitro-2-acetoxyethane

3-acetylmercaptocycloheptene

sodium

→

3-[2-nitroethylthio]cycloheptene

Ausbeute 99.4%

Lösungsmittel

ethanol

ethanol

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux for 15 minutes
2. 2
   TemperaturThe solution was then cooled to 0°
3. 3
   Sonstigewas partitioned between 1 N HCl and methylene chloride
4. 4
   ExtraktionThe aqueous phase was further extracted with methylene chloride
5. 5
   Trocknendried over sodium sulfate
6. 6
   Sonstigeevaporated

Vorschrift

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.

Quelle