Reaktion #5761

Reaktionsgleichung

farnesol

2-(diethylphosphono)isovaleronitrile

potassium bis(trimethylsilyl)amide

water

→

2 -(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile

Ausbeute 96.0%

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe cooling bath was removed
2. 2
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 30 minutes
3. 3
   TemperaturThe reaction mixture was cooled to -70° C. again
4. 4
   workup.STIRRINGwith stirring
5. 5
   Temperaturto warm to room temperature
6. 6
   Sonstigethe organic layer was separated
7. 7
   Waschenwashed with saturated aqueous sodium bicarbonate
8. 8
   Trocknensaturated aqueous sodium chloride, and dried over MgSO4
9. 9
   SonstigeThe organic layer was separated from MgSO4 by filtration
10. 10
    Einengenconcentrated
11. 11
    Sonstigeto give a residue, which
12. 12
    Sonstigewas purified with silica gel column chromatography (solvent: n-hexane/ethyl acetate=100:1)

Vorschrift

To a solution of 2-(diethylphosphono)isovaleronitrile (8.72 g, 40 mmol) in toluene (75 ml) was gradually added a 0.5 M solution of potassium bis(trimethylsilyl)amide in toluene (75 ml) with stirring at -70° C. under argon atmosphere. The cooling bath was removed, and the reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was cooled to -70° C. again, and farnesol (5.88 g, 26.7 mmol) was added thereto with stirring, and the mixture was allowed to warm to room temperature. After addition of water, the organic layer was separated, washed with saturated aqueous sodium bicarbonate and then saturated aqueous sodium chloride, and dried over MgSO4. The organic layer was separated from MgSO4 by filtration and concentrated to give a residue, which was purified with silica gel column chromatography (solvent: n-hexane/ethyl acetate=100:1) to obtain the aimed 2 -(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile (7.23 g, 96%; 2Z:2E=25.6:1).

Quelle