Reacción #50477

Ecuación de reacción

3,7,11-trimethyl-2,6,10-tridecatrien-1-ol

N-chlorosuccinimide

dimethyl sulfide

→

colorless liquid

Rendimiento 85.0%

(E,E)-1-Chloro-3,7,11-trimethyl-2,6,10-dodecatriene

Rendimiento 85.0%

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaby cooling to -40° C
2. 2
   Temperaturato warm gradually to 0° C. over 1 hour
3. 3
   Temperaturamaintained for 1 hour
4. 4
   OtroAfter quenching with cold water
5. 5
   Extracciónthe mixture was extracted with hexane
6. 6
   Extracciónthe hexane extract
7. 7
   Lavadowas washed with cold water and cold brine
8. 8
   Secadodried (MgSO4)
9. 9
   Otroevaporated
10. 10
    Otroto afford 483 mg of a crude product
11. 11
    LavadoRapid flash chromatography on 20 g of silica gel eluted with 3:97 ethyl acetate

Procedimiento

(Note: all temperatures indicated are for the contents of the reaction flask). To a stirred solution of 299 mg (2.24 mmol) of N-chlorosuccinimide in 15 mL of dichloromethane at -30° C. under argon was added 0.18 mL (2.45 mmol) of distilled dimethyl sulfide over 5 minutes. After 10 minutes at -30° C., the reaction was allowed to warm to 0° C. for 10 minutes, followed by cooling to -40° C. A solution of 441.4 mg (1.99 mmol) of 3,7,11-trimethyl-2,6,10-tridecatrien-1-ol in 5 mL of dichloromethane was added dropwise over 10 minutes. The reaction was allowed to warm gradually to 0° C. over 1 hour, and then maintained for 1 hour. After quenching with cold water, the mixture was extracted with hexane and the hexane extract was washed with cold water and cold brine, dried (MgSO4) and evaporated to afford 483 mg of a crude product. Rapid flash chromatography on 20 g of silica gel eluted with 3:97 ethyl acetate:petroleum ether provided 406.5 mg (85%) of a colorless liquid. 13C NMR indicated that this material contained a trace (3%) impurity.

Fuente