反应 #632068

反应方程式

4-fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole-3-carboxaldehyde

ammonium chloride

1-bromo-4-difluoromethylbenzene

magnesium

magnesium

→

4-(difluoromethyl)phenyl 4-fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indol-3-yl methanol

溶剂

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

反应条件

后处理

1. 1
   温度The mixture was warmed with a dryer
2. 2
   workup.STIRRINGThe mixture was stirred at same temperature for 1 hour
3. 3
   萃取The resultant mixture was extracted with ethyl acetate (50 ml) 3 times
4. 4
   干燥the combined organic layer was dried over magnesium sulfate
5. 5
   过滤The insoluble materials were filtered off
6. 6
   其他the filtrate was evaporated under reduced pressure

实验过程

To a mixture of magnesium turnings (71 mg) in tetrahydrofuran (2 ml) was added dropwise a solution of 1-bromo-4-difluoromethylbenzene (587 mg) in tetrahydrofuran (1.5 ml) under being stirred vigorously. The mixture was warmed with a dryer, and thereto was added 1,2-dibromoethane (4 drops). The resultant mixture was vigorously stirred at room temperature till a disappearance of magnesium turnings, and then dropwise added to a solution of the above 4-fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole-3-carboxaldehyde (350 mg) in tetrahydrofuran (4 ml) over 10 minutes at −78° C. under argon atmosphere. The mixture was stirred at same temperature for 1 hour, and thereto was added a saturated aqueous ammonium chloride solution (20 ml). The resultant mixture was extracted with ethyl acetate (50 ml) 3 times, and the combined organic layer was dried over magnesium sulfate. The insoluble materials were filtered off, and the filtrate was evaporated under reduced pressure to give crude 4-(difluoromethyl)phenyl 4-fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indol-3-yl methanol, which was used in the subsequent step without further purification.

来源