Реакция #75599

Уравнение реакции

(2S)-1-(trityloxy)-5-vinyl-6-heptene-2,5-diol

toluenesulfonyl chloride

water

→

(5R)-5-[(trityloxy)methyl]-2,2-divinyltetrahydrofuran

Выход 47.3%

Растворители

pyridine

Условия реакции

Обработка

1. 1
   workup.STIRRINGit was stirred at room temperature for 10 min
2. 2
   ЭкстракцияAfter extracting twice with ethyl acetate
3. 3
   Промывкаwashed with brine
4. 4
   Сушкаdried over magnesium sulfate
5. 5
   ДругоеThe solvent was removed
6. 6
   workup.DISSOLUTIONthe resulting residue was dissolved in toluene
7. 7
   ДругоеAfter the solvent was removed again
8. 8
   Другоеthe resulting residue was purified by silica gel column chromatography

Методика

13.0 g of (2S)-1-(trityloxy)-5-vinyl-6-heptene-2,5-diol and 57.2 g of toluenesulfonyl chloride were dissolved in 200 ml pyridine, and stirred at 80° C. overnight. After the reaction was completed, water was added thereto, and it was stirred at room temperature for 10 min. After extracting twice with ethyl acetate, washed with brine, and dried over magnesium sulfate. The solvent was removed, and the resulting residue was dissolved in toluene. After the solvent was removed again, the resulting residue was purified by silica gel column chromatography to give 5.88 g of (5R)-5-[(trityloxy)methyl]-2,2-divinyltetrahydrofuran.

Источник