Реакция #54858

Уравнение реакции

2,5-dimethoxytetrahydrofuran

acetic acid

acetic acid

sodium acetate

glycine

→

title compound

Выход 33.6%

(1-Pyrryl)acetic Acid

Выход 33.6%

Растворители

toluene

Условия реакции

Обработка

1. 1
   ДругоеTo a 1 liter flask fitted with a condenser, a magnetic stirrer and a nitrogen inlet tube
2. 2
   ДругоеThe system is purged with nitrogen
3. 3
   Температураa positive nitrogen pressure is maintained
4. 4
   Температураthe solution is heated to reflux
5. 5
   Температураrefluxing
6. 6
   Другоеis removed under vacuum
7. 7
   Экстракцияextracted with four portions of ether
8. 8
   ПромывкаThe ether extracts are washed with water
9. 9
   Сушкаdried over anhydrous magnesium sulfate
10. 10
    Фильтрацияfiltered
11. 11
    Другоеthe ether is evaporated
12. 12
    Другоеto yield a slurry
13. 13
    Фильтрацияfiltered through celite
14. 14
    Другоеcrystallized
15. 15
    Температураby cooling
16. 16
    Другоеto give 8.41g

Методика

To a 1 liter flask fitted with a condenser, a magnetic stirrer and a nitrogen inlet tube is added acetic acid (glacial, 300 ml) and sodium acetate (32.8g; 0.4 mole). The system is purged with nitrogen and a positive nitrogen pressure is maintained. Then glycine (15.0g; 0.2 mole) is added and the solution is heated to reflux. To the refluxing, clear solution is added 2,5-dimethoxytetrahydrofuran (29 ml, 0.2 mole) over a period of 2 - 3 minutes; refluxing is continued an additional 2 minutes. The reaction mixture is cooled in an ice bath and most of the acetic acid is removed under vacuum. The residue is taken up in water and extracted with four portions of ether. The ether extracts are washed with water, dried over anhydrous magnesium sulfate, filtered and the ether is evaporated to yield a slurry. The slurry is taken up into toluene, filtered through celite and crystallized by cooling to give 8.41g. (33.6%) of the title compound. M.P. 88°-90° C.

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