반응 #50477

반응 방정식

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

N-chlorosuccinimide

dimethyl sulfide

→

colorless liquid

수율 85.0%

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

수율 85.0%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   온도by cooling to -40° C
2. 2
   온도to warm gradually to 0° C. over 1 hour
3. 3
   온도maintained for 1 hour
4. 4
   기타After quenching with cold water
5. 5
   추출the mixture was extracted with hexane
6. 6
   추출the hexane extract
7. 7
   세척was washed with cold water and cold brine
8. 8
   건조dried (MgSO4)
9. 9
   기타evaporated
10. 10
    기타to afford 483 mg of a crude product
11. 11
    세척Rapid flash chromatography on 20 g of silica gel eluted with 3:97 ethyl acetate

실험 절차

(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.

출처