Reacción #8675

Ecuación de reacción

p-toluenesulfonyl chloride

2,5-bis(hydroxymethyl)tetrahydrofuran

→

2,5-Anhydro-3,4-dideoxy-1,6-bis-O-[(4-methylphenyl)sulfonyl]hexitol

Disolventes

pyridine

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónthe precipitate is filtered off with suction
2. 2
   Lavadowashed with dichloromethane
3. 3
   Lavadowashed with dilute hydrochloric acid
4. 4
   Secadowith saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate
5. 5
   Otroevaporated to dryness
6. 6
   OtroThe crude product is recrystallized from ethanol

Procedimiento

34.0 g (261 mmol) of 2,5-bis(hydroxymethyl)tetrahydrofuran are dissolved in 260 ml of dichloromethane. A solution of 99.0 g (521 mmol) of p-toluenesulfonyl chloride in 52 ml of pyridine and 130 ml of dichloromethane is added dropwise thereto. After stirring at room temperature for 24 hours, the precipitate is filtered off with suction and washed with dichloromethane. The filtrate and the washing phases are combined, washed with dilute hydrochloric acid and then with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate and evaporated to dryness. The crude product is recrystallized from ethanol.

Fuente