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0 °C

Sodium hydride (2.2 g of 50% w/w slurry in mineral oil, 47.0 mmol) was washed with hexane and dried under vacuum. Dimethylsulfoxide (40 mL) was added, and the mixture was stirred and cooled in an ice bath while a solution of benzyl cyanide (5.0 g, 42.7 mmol) in dimethyl-sulfoxide (10 mL) was added dropwise. The ice bath was removed, and the solution was allowed to stir for 4 hours. The deep red solution was then cooled again to 0° C., and a solution of 1-iodopentane (5.60 mL, 42.7 mmol) in dimethyl-sulfoxide (10 mL) was added dropwise. The mixture was stirred and allowed to come to ambient temperature over 12 hours. It was poured into water (200 mL), and extracted with ethyl acetate (2×200 mL). The extracts were washed in sequence with water (3×200 mL), then combined, dried over anhydrous magnesium sulfate, filtered and evaporated. The oily residue was separated by column chromatography (3:97 ethyl acetate-hexane) to afford the product, 2-phenylheptanenitrile, as a clear oil (4.41 g, 23.5 mmol, 55%).

1. customdried under vacuum
2. additionDimethylsulfoxide (40 mL) was added
3. additionwas added dropwise
4. customThe ice bath was removed
5. stirringto stir for 4 hours
6. stirringThe mixture was stirred
7. extractionextracted with ethyl acetate (2×200 mL)
8. washThe extracts were washed in sequence with water (3×200 mL)
9. dry with materialdried over anhydrous magnesium sulfate
10. filtrationfiltered
11. customevaporated
12. customThe oily residue was separated by column chromatography (3:97 ethyl acetate-hexane)