Reacción #335751

Ecuación de reacción

dimethylsulfide

N-chlorosuccinimide

(E,E)-farnesol

→

title compound

Rendimiento 103.8%

(E,E)-Farnesyl chloride

Rendimiento 103.8%

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe cooling bath was removed
2. 2
   TemperaturaThe mixture was cooled to -40 °
3. 3
   OtroThe cooling bath was removed
4. 4
   workup.STIRRINGthe mixture was stirred for 30 min
5. 5
   Otrorose to 0°
6. 6
   Otroa clear solution was obtained
7. 7
   Otrowas removed on a rotary evaporator
8. 8
   LavadoThe solution was washed with ice cold water (3×90 ml) and cold brine (2×35 ml)
9. 9
   Secadodried (MgSO4)
10. 10
    OtroThe solvent was removed under vacuum at ambient temperature
11. 11
    Otrofinally dried under pump vacuum

Procedimiento

A solution of N-chlorosuccinimide (6.8 g, 50.9 mmol) in dry dichloromethane (338 ml) was cooled to -30 ° and dimethylsulfide (4.1 ml, 55.3 mmol) was added dropwise over 3 min. After 13 min., the cooling bath was removed and the mixture was stirred for 30 min. The mixture was cooled to -40 ° and a solution of (E,E)-farnesol (11.3 ml, 44 mmol) in 112 ml dichloromethane was added over 10 min. The cooling bath was removed and the mixture was stirred for 30 min. The temperature of the reaction mixture rose to 0° and a clear solution was obtained. After stirring for two more hours the solvent (about 400 ml) was removed on a rotary evaporator and the material was taken up in hexane (600 ml). The solution was washed with ice cold water (3×90 ml) and cold brine (2×35 ml) and then dried (MgSO4). The solvent was removed under vacuum at ambient temperature and finally dried under pump vacuum to give 11.0 g (100%) of title compound as a pale yellow liquid.

Fuente