反応 #1904030

反応方程式

Pyridine

tris(2hydroxyethyl)methane

hydrochloric acid

methanesulphonyl chloride

→

tris[2-(methylsulphonyloxy)ethyl]methane

溶媒

dichloromethane

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   その他did not rise above 15° C
2. 2
   workup.ADDITIONwas then added drop-wise at such a rate that the temperature
3. 3
   その他did not rise above 15° C.
4. 4
   その他exothermic reaction
5. 5
   workup.WAITThe reaction was left
6. 6
   その他the layers separated
7. 7
   抽出The aqueous layer was extracted with further dichloromethane (50 ml)
8. 8
   乾燥dried over sodium sulphate
9. 9
   ろ過filtered
10. 10
    濃縮concentrated in vacuo

実験手順

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.

出典