Reacción #487277

Ecuación de reacción

N-Chlorosuccinimide

dimethyl sulphide

NaCl

farnesol

→

Compound ( b )

Rendimiento 89.0%

Farnesyl chloride

Rendimiento 89.0%

Disolventes

CH2Cl2

Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to 0° C. before it
2. 2
   Temperaturawas cooled to -40° C
3. 3
   workup.ADDITIONwas added dropwise to the mixture over a period of 3 minutes
4. 4
   Temperaturawas maintained for another hour
5. 5
   workup.ADDITIONwas poured into a separatory funnel which
6. 6
   ExtracciónThe aqueous layer was extracted with two 10 ml portions of pentane
7. 7
   Lavadowashed with two 5 ml portions of cold saturated NaCl
8. 8
   SecadoThe organic layer was dried over MgSO4
9. 9
   Concentraciónconcentrated to dryness in vacuo

Procedimiento

N-Chlorosuccinimide (0.66 g, 4.95 mmol) was dissolved in 20 ml of dry CH2Cl2 under a nitrogen atmosphere. The solution was cooled to -30° C. and 0.37 ml dimethyl sulphide (5 mmol) was added. The mixture was allowed to warm to 0° C. before it was cooled to -40° C. Then farnesol (1 g, 4.5 mmol) dissolved in 2.5 ml CH2 Cl2 was added dropwise to the mixture over a period of 3 minutes. The reaction mixture was warmed to 0.C in 1 h, at which temperature it was maintained for another hour. After 15 minutes of stirring at room temperature the reaction mixture was poured into a separatory funnel which contained 12.5 ml of cold saturated NaCl. The aqueous layer was extracted with two 10 ml portions of pentane. The organic layers were combined with an additional 10 ml of pentane and washed with two 5 ml portions of cold saturated NaCl. The organic layer was dried over MgSO4 and concentrated to dryness in vacuo. Compound (b) was thus obtained in a yield of 89%.

Fuente