Reaktion #481599

Reaktionsgleichung

thionyl chloride

4-hydroxyproline

ethanol

→

4hydroxy-L-proline ethyl ester hydrochloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeequipped with an addition funnel
2. 2
   TemperaturThe flask was then cooled in a dry ice/acetone bath
3. 3
   SonstigeThe funnel was removed
4. 4
   SonstigeThe flask was equipped with a reflux condenser and a sodium hydroxide trap
5. 5
   Temperaturthe mixture was refluxed for two hours
6. 6
   SonstigeThe product was precipitated in ether
7. 7
   Sonstigeisolated by filtration
8. 8
   Waschenwashed three times with ether
9. 9
   Sonstigeit was dried under a stream of nitrogen

Vorschrift

200 mL of absolute ethanol were placed in a 500-mL one-necked round-bottomed flask equipped with an addition funnel. The flask was then cooled in a dry ice/acetone bath, then 17 mL (0.23 mmoles) of thionyl chloride were added from the addition funnel over a 10 minute period. The funnel was removed, and 26.2 g (0.20 mmoles) of 4-hydroxyproline were added in one portion while stirring. The flask was equipped with a reflux condenser and a sodium hydroxide trap, and the mixture was refluxed for two hours. The product was precipitated in ether, isolated by filtration, and washed three times with ether, then it was dried under a stream of nitrogen followed by high vacuum.

Quelle