تفاعل #48112

معادلة التفاعل

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

4-trifluoromethoxy-phenylboronic acid

potassium carbonate

acetone

→

4-(β-D-glucopyranos-1-yl)-2-(4-trifluoromethoxy-benzyl)-benzonitrile

المذيبات

water

brine

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONAn Ar filled flask
2. 2
   درجة الحرارةis cooled in an ice-bath
3. 3
   workup.STIRRINGthe reaction mixture is stirred for 16 h at ambient temperature
4. 4
   استخلاصextracted with ethyl acetate
5. 5
   تجفيفThe combined extracts are dried over sodium sulfate
6. 6
   أخرىthe solvent is removed under reduced pressure
7. 7
   workup.DISSOLUTIONThe residue is dissolved in methanol (9 mL)
8. 8
   workup.ADDITIONtreated with 4 M aqueous potassium hydroxide solution (1 mL)
9. 9
   workup.STIRRINGThe resulting solution is stirred at ambient temperature for 1 h
10. 10
    أخرىThe methanol is evaporated
11. 11
    workup.ADDITIONthe residue is diluted with brine
12. 12
    استخلاصextracted with ethyl acetate
13. 13
    أخرىThe organic extracts collected
14. 14
    تجفيفare dried over sodium sulfate
15. 15
    أخرىthe solvent is removed
16. 16
    أخرىThe residue is chromatographed on silica gel (dichloromethane/methanol 1:0->8:1)

الإجراء التجريبي

An Ar filled flask is charged with 2-bromomethyl-4-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzonitrile (0.25 g), 4-trifluoromethoxy-phenylboronic acid (0.20 g), potassium carbonate (0.26) and a 3:1 mixture of degassed acetone and water (4 mL). The mixture is stirred at room temperature for 5 min, before it is cooled in an ice-bath. Then palladium dichloride (5 mg) is added and the reaction mixture is stirred for 16 h at ambient temperature. The mixture is then diluted with brine and extracted with ethyl acetate. The combined extracts are dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is dissolved in methanol (9 mL) and treated with 4 M aqueous potassium hydroxide solution (1 mL). The resulting solution is stirred at ambient temperature for 1 h and then neutralized with 1 M hydrochloric acid. The methanol is evaporated, and the residue is diluted with brine and extracted with ethyl acetate. The organic extracts collected are dried over sodium sulfate, and the solvent is removed. The residue is chromatographed on silica gel (dichloromethane/methanol 1:0->8:1).

المصدر