反応 #927227

反応方程式

2,3,3-trimethylindolenine

3-iodopropionic acid

→

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

反応条件

後処理

1. 1
   その他A 2-necked 50 milliliter round-bottomed flask equipped with a magnetic stirring bar and an argon inlet
2. 2
   workup.ADDITIONwas charged
3. 3
   その他precipitated out of solution
4. 4
   その他formed a highly viscous medium
5. 5
   温度Upon cooling
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   抽出the reaction mixture was extracted three times with 200 milliliter portions of diethyl ether
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   その他to remove all of the
8. 8
   workup.DISSOLUTIONThe remaining crystalline solid was then dissolved in 10 milliliters of water
9. 9
   抽出extracted three times with 50 milliliter portions of diethyl ether
10. 10
    抽出extracted three times with 25 milliliter portions of CHCl3
11. 11
    その他The aqueous layer was then removed
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    その他dried under vacuum (1.0 mm Hg) for 24 hours
13. 13
    その他The resulting amorphous solid was then recrystallized from toluene/CHCl3

実験手順

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:

出典