Hydrochloric Acid → 212382-64-4

Temperature

7.5 °C

Tosylmethyl isocyanide (3.0 g, 15.4 mmol) was dissolved in 15 mL of anhydrous dimethylsulfoxide and the solution was cooled to 5-10° C. in an ice water bath. Potassium tert-butoxide (5.03 g, 44.8 mmol) was then added and the solution turned dark brown in color. The reaction was allowed to warm to room temperature and stirred for 1 hour. A solution of the cyclohexanone (1) (1.62 g, 12.8 mmol) in anhydrous methanol (685 μL) was added to the reaction via syringe and the reaction was stirred at room temperature under argon for 40 hours. The reaction was then diluted with 25 mL of water and placed in an ice water bath and the reaction was made acidic by the dropwise addition of aqueous HCl (6.0 M, aq.). The aqueous phase was extracted 2 times with hexane, and the organic phases were combined and dried over MgSO4, filtered and concentrated to provide 2.24 g of a yellow mixture of oil and solid. The crude mixture was purified by chromatography on silica gel (eluted with 0-50% dichloromethane in hexanes) and the fractions were concentrated and monitored by IR to find 870 mg (50%) of the nitrile product (2) as a transparent oil.

1. temperatureto warm to room temperature
2. stirringthe reaction was stirred at room temperature under argon for 40 hours
3. customplaced in an ice water bath
4. extractionThe aqueous phase was extracted 2 times with hexane
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-76f0dab9543643d88a18e7a89cb20541

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06624309B1