反应 #50477

反应方程式

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

N-chlorosuccinimide

dimethyl sulfide

→

colorless liquid

收率 85.0%

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

收率 85.0%

溶剂

dichloromethane

dichloromethane

反应条件

后处理

1. 1
   温度by cooling to -40° C
2. 2
   温度to warm gradually to 0° C. over 1 hour
3. 3
   温度maintained for 1 hour
4. 4
   其他After quenching with cold water
5. 5
   萃取the mixture was extracted with hexane
6. 6
   萃取the hexane extract
7. 7
   洗涤was washed with cold water and cold brine
8. 8
   干燥dried (MgSO4)
9. 9
   其他evaporated
10. 10
    其他to afford 483 mg of a crude product
11. 11
    洗涤Rapid flash chromatography on 20 g of silica gel eluted with 3:97 ethyl acetate

实验过程

(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.

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