반응 #1052611

반응 방정식

1-(3-chloropropionyl)indoline-6-diazonium tetrafluoroborate

→

title compound

수율 95.0%

1-(3-Chloropropionyl)-6-fluoroindoline

수율 95.0%

용매

heptane

반응 조건

후처리

1. 1
   온도the suspension was heated
2. 2
   온도under reflux for 1 hour
3. 3
   workup.ADDITIONthe reaction product was poured into ice
4. 4
   추출The mixture was then extracted with 50 ml of ethyl acetate
5. 5
   추출the organic extract
6. 6
   세척was washed with 50 ml of water
7. 7
   건조after which it was dried over anhydrous magnesium sulfate
8. 8
   여과The mixture was filtered
9. 9
   기타the solvent was removed from the filtrate by distillation under reduced pressure
10. 10
    기타The resulting residue was purified by silica gel column chromatography
11. 11
    workup.ADDITIONby volume mixture of hexane and ethyl acetate as the eluent

실험 절차

1.23 g (3.8 mmol) of 1-(3-chloropropionyl)indoline-6-diazonium tetrafluoroborate [prepared as described in step (1) above] were suspended in 20 ml of heptane, and the suspension was heated under reflux for 1 hour. At the end of this time, the mixture was cooled to room temperature, and the reaction product was poured into ice. The mixture was then extracted with 50 ml of ethyl acetate, and the organic extract was washed with 50 ml of water, after which it was dried over anhydrous magnesium sulfate. The mixture was filtered, and then the solvent was removed from the filtrate by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 810 mg (3.6 mmol) of the title compound (yield: 95%).

출처