Diethyl Ether → 1-Phenylcyclopentanecarbonitrile

To a suspension of sodium hydride (60%) (7.5 g, 187.79 mmol) in dimethyl sulfoxide (100 mL) was added dropwise a mixture of phenyl acetonitrile (10 g, 85.36 mmol) and 1,4-dibromobutane (18.43 g, 187.79 mmol) dissolved in dimethyl sulfoxide: ether (120 mL, 1:1) at 0° C. Stirring was continued for 30 min at same temperature and at room temperature for 3 h. After completion of the reaction, the reaction mixture was quenched with 1N HCl (10 mL) and water (100 mL) was added. This mixture was extracted with ethyl acetate (3×100 mL), and the organic part separated and washed with water (3×100 mL) and brine (100 mL). The organic part was dried over sodium sulfate and concentrated to get a crude product which was purified on a CombiFlash column (eluted at 3% ethyl acetate in hexane) to afford 1-phenyl-cyclopentanecarbonitrile (276) (11.5 g, 78.68%) as a colorless liquid.

1. additionwas added dropwise
2. customat 0° C
3. customAfter completion of the reaction
4. customthe reaction mixture was quenched with 1N HCl (10 mL) and water (100 mL)
5. additionwas added
6. extractionThis mixture was extracted with ethyl acetate (3×100 mL)
7. customthe organic part separated
8. washwashed with water (3×100 mL) and brine (100 mL)
9. dry with materialThe organic part was dried over sodium sulfate
10. concentrationconcentrated
11. customto get a crude product which
12. customwas purified on a CombiFlash column (eluted at 3% ethyl acetate in hexane)

ORD record

ord-95ad4242774b46858f062900d6e1cf94

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045486B2