Hydrochloric Acid → 212382-64-4

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence