反应详情

Sodium hydride (13.3 g., 0.32 mol, 57% oil dispersion) was washed with pentane to remove the oil and 26.1 g. (0.275 mol) of 3-hydroxypyridine in 300 ml. of anhydrous DMF was added with cooling in a cold water bath. The mixture was then stirred and heated at 60° for 1 hour. After cooling to 25°, 40.7 g. (0.275 mol) of 4-bromobutyronitrile in 40 ml. of anhydrous DMF was added dropwise over 1 hour with cooling to keep the reaction temperature below 30°. The reaction mixture was then stirred at 25° for 17 hours and the solvent was removed in vacuo. The residue was treated with 100 ml. of water and the product was extracted with CH2Cl2. After washing the extract with 1N NaOH and then with H2O, it was dried (MgSO4) and concentrated in vacuo to an oil which was distilled to yield 25.1 g., b.p. 133°-135°/0.4 mm, (56% yield), of 4-(3-pyridinyloxy)butyronitrile.

1. customto remove the oil and 26.1 g
2. temperaturewith cooling in a cold water bath
3. temperatureheated at 60° for 1 hour
4. temperatureAfter cooling to 25°
5. temperaturewith cooling
6. customthe reaction temperature below 30°
7. stirringThe reaction mixture was then stirred at 25° for 17 hours
8. customthe solvent was removed in vacuo
9. additionThe residue was treated with 100 ml
10. extractionof water and the product was extracted with CH2Cl2
11. washAfter washing the
12. extractionextract with 1N NaOH
13. dry with materialwith H2O, it was dried (MgSO4)
14. concentrationconcentrated in vacuo to an oil which
15. distillationwas distilled
16. customto yield 25.1 g