반응 #928091

반응 방정식

potassium fluoride

6-bromooxindole

vinyltributylstannane

lithium chloride

→

6-vinyloxindole

수율 31.4%

용매

diethyl ether

ethyl acetate

acetonitrile

반응 조건

후처리

1. 1
   기타The resulting reaction
2. 2
   workup.STIRRINGwas stirred
3. 3
   온도with heating for 16 h
4. 4
   workup.ADDITIONThe reaction was poured into
5. 5
   workup.STIRRINGa vigorously stirring
6. 6
   여과The resulting biphashic mixture was filtered through a Celite 521 pad
7. 7
   기타the pad flushed with ethyl acetate (5×200 mL)
8. 8
   세척The combined organic phases were washed with water (200 mL), saturated sodium chloride (200 mL)
9. 9
   여과filtered through Whatman PS 1 paper
10. 10
    기타evaporated in vacuo to a golden yellow syrup
11. 11
    기타to yield several crops of tan solid
12. 12
    여과filtered
13. 13
    기타air dried

실험 절차

To a mixture of 6-bromooxindole (Procedure D, 0.50 g, 2.4 mmol), vinyltributylstannane (0.95 g, 3.0 mmol), lithium chloride (0.03 g, 7.1 mmol), 2,6-di-tert-butyl-4-methylphenol (0.01 g, 0.05 mmol) in acetonitrile (25 ml) stirring at 80° C. was added dichlorobis(triphenylphosphine)palladium (II). The resulting reaction was stirred with heating for 16 h. The reaction was poured into a vigorously stirring mixture of 5M potassium fluoride solution: ethyl acetate/ 1:1 (250 mL) and stirred for 0.75 h. The resulting biphashic mixture was filtered through a Celite 521 pad and the pad flushed with ethyl acetate (5×200 mL). The combined organic phases were washed with water (200 mL), saturated sodium chloride (200 mL) and filtered through Whatman PS 1 paper and evaporated in vacuo to a golden yellow syrup. The syrup was titurated with diethyl ether to yield several crops of tan solid. Pure samples were combined, slurried with diethyl ether, filtered, and air dried to yield 0.12 g (31%) of 6-vinyloxindole: 1H NMR (DMSO-d6): δ10.36 (s, 1H), 7.13 (d, 1H, J=7.7 Hz), 6.98 (d, 1H, J=7.5 Hz), 6.66 (dd, 1H, J=10.9, 17.7 Hz), 5.70 (d, 1H, J=17.6 Hz), 5.18 (d, 1H, J=10.9 Hz), 3.42 (s, 2H).

출처