反应详情

To a stirred solution of sodium cyanide (10.5 g, 0.214 mol) in H2O (20 mL) was added a solution of 2-(bromomethyl)naphthalene (40.0 g, 0.181 mol) in EtOH (170 mL). The resulting mixture was heated at reflux for 3 h, then spin-evaporated in vacuo. The residue was partitioned between H2O (175 mL) and CH2Cl2 (200 mL). The aqueous layer was further extracted with CH2Cl2 (3×200 mL). The combined organic layers were dried over MgSO4 (5 g) and spin-evaporated in vacuo to a solid. The solid was dissolved in refluxing EtOH (100 mL). The clarified solution was stored at 3° C. for 16 h. Solids were collected by filtration and dried to constant weight in vacuo to give 24.8 g (81.9%) of product suitable for further transformation. A total of 257.2 g of material was prepared in this fashion.

1. temperatureThe resulting mixture was heated
2. temperatureat reflux for 3 h
3. customspin-evaporated in vacuo
4. customThe residue was partitioned between H2O (175 mL) and CH2Cl2 (200 mL)
5. extractionThe aqueous layer was further extracted with CH2Cl2 (3×200 mL)
6. dry with materialThe combined organic layers were dried over MgSO4 (5 g)
7. customspin-evaporated in vacuo to a solid
8. dissolutionThe solid was dissolved
9. temperaturein refluxing EtOH (100 mL)
10. filtrationSolids were collected by filtration
11. customdried to constant weight in vacuo