Reaktion #75015

Reaktionsgleichung

sodium ethoxide

sodium

bromoacetaldehyde diethylacetal

3-acetylmercaptocycloheptene

→

3-[(2,2-diethoxyethyl)thio]-1-cycloheptene

Ausbeute 99.4%

Lösungsmittel

ethanol

ethanol

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was heated
2. 2
   Temperaturunder reflux for 15 minutes
3. 3
   TemperaturThe reaction mixture was heated
4. 4
   Temperaturunder reflux for 2.0 hours
5. 5
   Temperaturcooled
6. 6
   FiltrationThe precipitated sodium bromide was filtered
7. 7
   Waschenwashed well with absolute ethanol
8. 8
   EinengenThe filtrate was concentrated
9. 9
   Sonstigethe residue partitioned between ether/brine
10. 10
    ExtraktionThe aqueous phase was further extracted with ether
11. 11
    Trocknendried over magnesium sulfate
12. 12
    Sonstigeevaporated

Vorschrift

A solution of fresh sodium ethoxide prepared from 7.6 g (0.330 gram-atom metallic sodium) in 200 ml of absolute ethanol was treated dropwise with 56.18 g (0.330 mole) of 3-acetylmercaptocycloheptene in 10 ml of absolute ethanol. The reaction was heated under reflux for 15 minutes and then cooled to room temperature. A solution of 49.69 ml (0.330 mole) of bromoacetaldehyde diethylacetal in 30 ml of absolute ethanol was added dropwise. The reaction mixture was heated under reflux for 2.0 hours and cooled. The precipitated sodium bromide was filtered and washed well with absolute ethanol. The filtrate was concentrated and the residue partitioned between ether/brine. The aqueous phase was further extracted with ether. The organic extracts were pooled, dried over magnesium sulfate, and evaporated to afford 80.1 g (0.328 mole, 99%) of pure 3-[(2,2-diethoxyethyl)thio]-1-cycloheptene, as a colorless oil.

Quelle