Reaktion #5759

Reaktionsgleichung

geranial

2-(diethylphosphono)isovaleronitrile

potassium bis(trimethylsilyl)amide

water

→

2-(1-methylethyl)-5,9-dimethyl-2,4,8-decatrienenitrile

Ausbeute 90.0%

Lösungsmittel

n-hexane ethyl acetate

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGwith continuous stirring at the same temperature
2. 2
   Temperaturthe reaction mixture was warmed up to room temperature
3. 3
   Extraktionthe organic layer was extracted
4. 4
   ExtraktionThe organic extract
5. 5
   Waschenwas washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
6. 6
   Trocknendried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   EinengenThe filtrate was concentrated
9. 9
   Sonstigeto give a residue, which

Vorschrift

To a solution of 2-(diethylphosphono)isovaleronitrile (6.54 g, 30 mmol) in toluene (55 ml) was added a 0.5 M solution of potassium bis(trimethylsilyl)amide in toluene (56 ml) with stirring on a cooling bath at -70° C. After 30 minutes, geranial (3.80 g, 25 mmol) was added thereto with continuous stirring at the same temperature, and then the reaction mixture was warmed up to room temperature. After addition of water to the mixture, the organic layer was extracted. The organic extract was washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over MgSO4, and filtered. The filtrate was concentrated to give a residue, which was then subjected to silica gel column chromatography (solvent: n-hexane/ethyl acetate=100:1) to give 2-(1-methylethyl)-5,9-dimethyl-2,4,8-decatrienenitrile (4.87 g, 90%, 2Z:2E=22.4:1).

Quelle