Реакция #3176

Уравнение реакции

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

pyridine

dichloromethane

(±)-2-chloropropionyl chloride

→

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

Растворители

water

Условия реакции

Обработка

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

Методика

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.

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