Réaction #1244283

Équation de réaction

(S)-1,4-pentanediol

triethylamine

methanesulfonyl chloride

→

(S)-1,4-bis(methanesulfonyloxy)pentane

Rendement 98.0%

Solvants

ethyl acetate

Conditions de réaction

Traitement

1. 1
   LavageThe solution was washed
2. 2
   workup.ADDITIONby adding 15 mL of a saturated aqueous solution of sodium hydrogencarbonate
3. 3
   LavageThe organic layer was further washed with 15 mL of water
4. 4
   Séchagewas dried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONThe solvent was then distilled off under a reduced pressure

Mode opératoire

A solution containing 2.5 g (24 mmol) of (S)-1,4-pentanediol produced in Example 3, 7.3 g (72 mmol) of triethylamine, and 30 mL of ethyl acetate was cooled to 5° C. Subsequently, 6.6 g (58 mmol) of methanesulfonyl chloride was added to the solution, and the solution was stirred for one hour. The solution was washed by adding 15 mL of a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was further washed with 15 mL of water, and was dried over anhydrous magnesium sulfate. The solvent was then distilled off under a reduced pressure. Thus, (S)-1,4-bis(methanesulfonyloxy)pentane was obtained as a light yellow oily substance (6.1 g, yield; 98%).

Source