反応 #1365697

反応方程式

Ascorbic acid

cesium carbonate

benzyl bromide

→

3-O-benzyl ascorbic acid

収率 48.0%

溶媒

dimethylsulfoxide

dichloromethane

反応条件

後処理

1. 1
   温度The reaction mixture was cooled down to the room temperature
2. 2
   その他to produce a solid
3. 3
   ろ過After filtration
4. 4
   濃縮the filtrate was concentrated under reduced pressure
5. 5
   その他purified by column chromatography on silica gel

実験手順

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%).

出典