تفاعل #928091

معادلة التفاعل

potassium fluoride

6-bromooxindole

vinyltributylstannane

lithium chloride

→

6-vinyloxindole

المردود 31.4%

المذيبات

diethyl ether

ethyl acetate

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   أخرىThe resulting reaction
2. 2
   workup.STIRRINGwas stirred
3. 3
   درجة الحرارةwith heating for 16 h
4. 4
   workup.ADDITIONThe reaction was poured into
5. 5
   workup.STIRRINGa vigorously stirring
6. 6
   ترشيحThe resulting biphashic mixture was filtered through a Celite 521 pad
7. 7
   أخرىthe pad flushed with ethyl acetate (5×200 mL)
8. 8
   غسيلThe combined organic phases were washed with water (200 mL), saturated sodium chloride (200 mL)
9. 9
   ترشيحfiltered through Whatman PS 1 paper
10. 10
    أخرىevaporated in vacuo to a golden yellow syrup
11. 11
    أخرىto yield several crops of tan solid
12. 12
    ترشيحfiltered
13. 13
    أخرىair dried

الإجراء التجريبي

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).

المصدر