反应 #487277

反应方程式

N-Chlorosuccinimide

dimethyl sulphide

NaCl

farnesol

→

Compound ( b )

收率 89.0%

Farnesyl chloride

收率 89.0%

溶剂

CH2Cl2

Cl2

反应条件

后处理

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

实验过程

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%.

来源