Reaktion #1244283

Reaktionsgleichung

(S)-1,4-pentanediol

triethylamine

methanesulfonyl chloride

→

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

Ausbeute 98.0%

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle