Reaction #1904030

Reaction equation

Pyridine

tris(2hydroxyethyl)methane

hydrochloric acid

methanesulphonyl chloride

→

tris[2-(methylsulphonyloxy)ethyl]methane

Solvents

dichloromethane

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Otherdid not rise above 15° C
2. 2
   workup.ADDITIONwas then added drop-wise at such a rate that the temperature
3. 3
   Otherdid not rise above 15° C.
4. 4
   Otherexothermic reaction
5. 5
   workup.WAITThe reaction was left
6. 6
   Otherthe layers separated
7. 7
   ExtractionThe aqueous layer was extracted with further dichloromethane (50 ml)
8. 8
   Dryingdried over sodium sulphate
9. 9
   Filtrationfiltered
10. 10
    Concentrationconcentrated in vacuo

Procedure

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.

Source