Реакция #1904030

Уравнение реакции

Pyridine

tris(2hydroxyethyl)methane

hydrochloric acid

methanesulphonyl chloride

→

tris[2-(methylsulphonyloxy)ethyl]methane

Растворители

dichloromethane

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   Другоеdid not rise above 15° C
2. 2
   workup.ADDITIONwas then added drop-wise at such a rate that the temperature
3. 3
   Другоеdid not rise above 15° C.
4. 4
   Другоеexothermic reaction
5. 5
   workup.WAITThe reaction was left
6. 6
   Другоеthe layers separated
7. 7
   ЭкстракцияThe aqueous layer was extracted with further dichloromethane (50 ml)
8. 8
   Сушкаdried over sodium sulphate
9. 9
   Фильтрацияfiltered
10. 10
    Концентрированиеconcentrated in vacuo

Методика

To an stirred ice-cooled solution of tris(2hydroxyethyl)methane (10 g, 0.0676 mol) in dichloromethane (50 ml) was slowly dripped a solution of methanesulphonyl chloride (40 g, 0.349 mol) in dichloromethane (50 ml) under nitrogen at such a rate that the temperature did not rise above 15° C. Pyridine (21.4 g, 0.27 mol, 4 eq) dissolved in dichloromethane (50 ml) was then added drop-wise at such a rate that the temperature did not rise above 15° C., exothermic reaction. The reaction was left to stir at room temperature for 24 h and then treated with 5 N hydrochloric acid solution (80 ml) and the layers separated. The aqueous layer was extracted with further dichloromethane (50 ml) and the organic extracts combined, dried over sodium sulphate, filtered and concentrated in vacuo to give tris[2-(methylsulphonyloxy)ethyl]methane contaminated with excess methanesulphonyl chloride. The theoretical yield was 25.8 g.

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