Reacción #54858

Ecuación de reacción

2,5-dimethoxytetrahydrofuran

acetic acid

acetic acid

sodium acetate

glycine

→

title compound

Rendimiento 33.6%

(1-Pyrryl)acetic Acid

Rendimiento 33.6%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroTo a 1 liter flask fitted with a condenser, a magnetic stirrer and a nitrogen inlet tube
2. 2
   OtroThe system is purged with nitrogen
3. 3
   Temperaturaa positive nitrogen pressure is maintained
4. 4
   Temperaturathe solution is heated to reflux
5. 5
   Temperaturarefluxing
6. 6
   Otrois removed under vacuum
7. 7
   Extracciónextracted with four portions of ether
8. 8
   LavadoThe ether extracts are washed with water
9. 9
   Secadodried over anhydrous magnesium sulfate
10. 10
    Filtraciónfiltered
11. 11
    Otrothe ether is evaporated
12. 12
    Otroto yield a slurry
13. 13
    Filtraciónfiltered through celite
14. 14
    Otrocrystallized
15. 15
    Temperaturaby cooling
16. 16
    Otroto give 8.41g

Procedimiento

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.

Fuente