반응 #927227

반응 방정식

2,3,3-trimethylindolenine

3-iodopropionic acid

→

N-(2-carboxyethyl)-2,3,3-trimethylindolinium iodide

반응 조건

후처리

1. 1
   기타A 2-necked 50 milliliter round-bottomed flask equipped with a magnetic stirring bar and an argon inlet
2. 2
   workup.ADDITIONwas charged
3. 3
   기타precipitated out of solution
4. 4
   기타formed a highly viscous medium
5. 5
   온도Upon cooling
6. 6
   추출the reaction mixture was extracted three times with 200 milliliter portions of diethyl ether
7. 7
   기타to remove all of the
8. 8
   workup.DISSOLUTIONThe remaining crystalline solid was then dissolved in 10 milliliters of water
9. 9
   추출extracted three times with 50 milliliter portions of diethyl ether
10. 10
    추출extracted three times with 25 milliliter portions of CHCl3
11. 11
    기타The aqueous layer was then removed
12. 12
    기타dried under vacuum (1.0 mm Hg) for 24 hours
13. 13
    기타The resulting amorphous solid was then recrystallized from toluene/CHCl3

실험 절차

A 2-necked 50 milliliter round-bottomed flask equipped with a magnetic stirring bar and an argon inlet was charged with re-distilled (pressure 2 mm Hg, temperature 45° C.) 2,3,3-trimethylindolenine (7.95 grams, 50.0 mmol) and 3-iodopropionic acid (2.00 grams, 10 mmol). The mixture was heated to 80° C. for 12 hours, during which time the product precipitated out of solution and formed a highly viscous medium. Upon cooling, the reaction mixture was extracted three times with 200 milliliter portions of diethyl ether to remove all of the unreacted starting material. The remaining crystalline solid was then dissolved in 10 milliliters of water, extracted three times with 50 milliliter portions of diethyl ether, and extracted three times with 25 milliliter portions of CHCl3. The aqueous layer was then removed and dried under vacuum (1.0 mm Hg) for 24 hours. The resulting amorphous solid was then recrystallized from toluene/CHCl3 mixtures to produce the N-(2-carboxyethyl)-2,3,3-trimethylindolinium iodide product as 3.0 grams of a yellow solid (83.5 percent yield). 1H and 13C NMR spectra indicated the following:

출처