Reacción #1365697

Ecuación de reacción

Ascorbic acid

cesium carbonate

benzyl bromide

→

3-O-benzyl ascorbic acid

Rendimiento 48.0%

Disolventes

dimethylsulfoxide

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was cooled down to the room temperature
2. 2
   Otroto produce a solid
3. 3
   FiltraciónAfter filtration
4. 4
   Concentraciónthe filtrate was concentrated under reduced pressure
5. 5
   Otropurified by column chromatography on silica gel

Procedimiento

Ascorbic acid (10 g, 56.8 mmol) was dissolved in 60 ml of dimethylsulfoxide, followed by addition of cesium carbonate (9.25 g, 28.4 mmol). After 20 minutes, benzyl bromide (6.75 ml, 56.8 mmol) was added to the reaction mixture and heated to 50° C. for 18 hours. The reaction mixture was cooled down to the room temperature and diluted with 150 ml of dichloromethane to produce a solid. After filtration, the filtrate was concentrated under reduced pressure and purified by column chromatography on silica gel to give 7.2 g of the 3-O-benzyl ascorbic acid (yield 48%).

Fuente