Reacción #5761

Ecuación de reacción

farnesol

2-(diethylphosphono)isovaleronitrile

potassium bis(trimethylsilyl)amide

water

→

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

Rendimiento 96.0%

Disolventes

toluene

toluene

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente