Réaction #3176

Équation de réaction

(±)-(3R,4S)-3-hydroxy-4-methylcarbonyloxytetrahydrofuran

pyridine

dichloromethane

(±)-2-chloropropionyl chloride

→

(±)-(3R,4S)-4-Acetoxy-3-(2-chloropropionyloxy)tetrahydrofuran

Solvants

water

Conditions de réaction

Traitement

1. 1
   Températurecooled
2. 2
   workup.ADDITIONAfter addition
3. 3
   AutreThe organic phase was then separated off
4. 4
   Lavagewashed twice with 50 ml of water each time
5. 5
   Séchagedried over sodium sulfate
6. 6
   Concentrationfinally concentrated
7. 7
   workup.DISTILLATIONThe crude product was purified by distillation at a pressure of 10 mbar

Mode opératoire

12.4 g of (±)-2-chloropropionyl chloride were added dropwise at 0°-5° C. to an ice-cooled mixture of 15.0 g of (±)-(3R,4S)-3-hydroxy-4-methylcarbonyloxytetrahydrofuran, 8.1 g of anhydrous pyridine and 200 ml of anhydrous dichloromethane. After addition was complete, the reaction mixture was stirred at 23° C. for a further 4 hours, after which it was poured onto 400 ml of water. The organic phase was then separated off, washed twice with 50 ml of water each time, dried over sodium sulfate and finally concentrated. The crude product was purified by distillation at a pressure of 10 mbar.

Source