反应详情

To a stirred suspension of sodium hydride (60% dispersed in oil) (4 g, 0.1 m) in DMSO (70 mL) under nitrogen at 15° C. was added dropwise a solution of 2-pyridyl acetonitrile (6 g, 51 mmol) and 1,5-dibromopentane (6.81 mL, 51 mmol) in ether (40 mL) and DMSO (10 mL) over 1 hour. The mixture was allowed to warm to room temperature and stirred for a further 24 hours under nitrogen. The reaction mixture was carefully quenched by the addition dropwise of isopropanol (10 mL), followed by water (100 mL) 10 minutes later. The reaction solution was taken up in EtOAc and washed with water. The aqueous layer was re-extracted with EtOAc, and the two organic layers were combined, dried (MgSO4), and concentrated in vacuo. The residue was purified on silica with a gradient of heptane to 9:1 heptane/EtOAc to give 1-cyano-1-(2-pyridyl)cyclohexane (6.77 g, 72%).

1. customThe reaction mixture was carefully quenched by the addition dropwise of isopropanol (10 mL)
2. customfollowed by water (100 mL) 10 minutes
3. washwashed with water
4. extractionThe aqueous layer was re-extracted with EtOAc
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo
7. customThe residue was purified on silica with a gradient of heptane to 9:1 heptane/EtOAc