反応 #48103

反応方程式

hydrobromic acid

2-phenyloxymethyl-4-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzonitrile

acetic anhydride

potassium carbonate

→

2-Bromomethyl-4-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzonitrile

溶媒

acetic acid

acetic acid

反応条件

後処理

1. 1
   温度cooled in an ice-bath
2. 2
   抽出the resultant mixture is extracted with ethyl acetate
3. 3
   乾燥The combined organic extracts are dried over sodium sulfate
4. 4
   その他the solvent is removed under reduced pressure
5. 5
   その他the precipitate is separated by filtration
6. 6
   その他dried at 50° C.
7. 7
   その他to give the pure product

実験手順

A 33% solution of hydrobromic acid in acetic acid (15 mL) is added to a solution of 2-phenyloxymethyl-4-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzonitrile (0.71 g) and acetic anhydride (0.12 mL) in acetic acid (10 ml). The resulting solution is stirred at 55° C. for 6 h and then cooled in an ice-bath. The reaction mixture is neutralized with chilled aqueous potassium carbonate solution, and the resultant mixture is extracted with ethyl acetate. The combined organic extracts are dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is taken up in ethyl aceate/cyclohexane (1:5), and the precipitate is separated by filtration and dried at 50° C. to give the pure product.

出典