反应详情

温度

0 °C

Chlorotrimethylsilyl (22 g) is added dropwise over 20 minutes to a suspension of NaI (30 g) in CH3CN (300 ml) cooled to 0° C. Stirring is continued for 30 minutes at room temperature. 2-Fluoromethyl2-phthalimido-5-benzyloxypentanenitrile (25 g) in CH3CN (50 ml) is added, and the mixture is stirred overnight at room temperature. This mixture is then poured into cold water containing sodium bicarbonate and sodium thiosulfate, and extracted with diethyl ether. The organic layer is dried over MgSO4 and concentrated in vacuo. The residue is taken up in THF (200 l) and triethylamine (7 g) is added. After stirring for 1 hour, the mixture is poured into water and extracted with diethyl ether. The organic layer is washed with H2O, dried over MgSO4, and concentrated in vacuo. The residue, a mixture of 2-fluoromethyl-2-phthalimido-5-hydroxypentanenitrile and 2-fluoromethyl-2-phthalimido-5-iodopentanenitrile is taken up in CH3CN (50 ml) and added to a solution of iodotrimethylsilyl prepared as described above from TMS Cl (22 g) and NaI (30 g) in CH3CH (300 ml). The mixture is stirred overnight at room temperature. Then it is poured into cold water containing sodium bicarbonate and sodium thiosulfate, and extracted with diethyl ether. The residue obtained after concentration of the organic layer in vacuo is filtered on a florisil column (30 g). Elution with diethyl ether and removal of the solvent under reduced pressure gives 22 g of 2-fluoromethyl-2-phthalimido-5-iodopentanenitrile as an oil.

1. stirringthe mixture is stirred overnight at room temperature
2. extractionextracted with diethyl ether
3. dry with materialThe organic layer is dried over MgSO4
4. concentrationconcentrated in vacuo
5. additiontriethylamine (7 g) is added
6. stirringAfter stirring for 1 hour
7. additionthe mixture is poured into water
8. extractionextracted with diethyl ether
9. washThe organic layer is washed with H2O
10. dry with materialdried over MgSO4
11. concentrationconcentrated in vacuo
12. additionThe residue, a mixture of 2-fluoromethyl-2-phthalimido-5-hydroxypentanenitrile and 2-fluoromethyl-2-phthalimido-5-iodopentanenitrile
13. additionadded to a solution of iodotrimethylsilyl
14. customprepared
15. stirringThe mixture is stirred overnight at room temperature
16. extractionextracted with diethyl ether
17. customThe residue obtained after concentration of the organic layer in vacuo
18. filtrationis filtered on a florisil column (30 g)
19. washElution
20. customwith diethyl ether and removal of the solvent under reduced pressure