Réaction #54858

Équation de réaction

2,5-dimethoxytetrahydrofuran

acetic acid

acetic acid

sodium acetate

glycine

→

title compound

Rendement 33.6%

(1-Pyrryl)acetic Acid

Rendement 33.6%

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   AutreTo a 1 liter flask fitted with a condenser, a magnetic stirrer and a nitrogen inlet tube
2. 2
   AutreThe system is purged with nitrogen
3. 3
   Températurea positive nitrogen pressure is maintained
4. 4
   Températurethe solution is heated to reflux
5. 5
   Températurerefluxing
6. 6
   Autreis removed under vacuum
7. 7
   Extractionextracted with four portions of ether
8. 8
   LavageThe ether extracts are washed with water
9. 9
   Séchagedried over anhydrous magnesium sulfate
10. 10
    Filtrationfiltered
11. 11
    Autrethe ether is evaporated
12. 12
    Autreto yield a slurry
13. 13
    Filtrationfiltered through celite
14. 14
    Autrecrystallized
15. 15
    Températureby cooling
16. 16
    Autreto give 8.41g

Mode opératoire

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.

Source