Reacción #3176

Ecuación de reacción

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

pyridine

dichloromethane

(±)-2-chloropropionyl chloride

→

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

Disolventes

water

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente