Hydrochloric Acid → HCID 11039804, compound

Participants

Reaction Steps

1.94 ml of a 1.4 molar solution of n-butyllithium (2.71 mmol) in pentane were added dropwise at 0° C. under argon for 2 min to a stirred solution of 500 mg (2.71 mmol) 3-tert-butyl-2,2-dimethylhex-5-en-3-ol in 4 ml THF. The solution obtained was stirred for 15 minutes, a solution of 370 mg (2.71 mmol) ZnCl2 in 2 ml THF and then 278 μl (2.71 mmol) benzonitrile were added. The reaction mixture was heated to room temperature and stirred for 1 hour. Subsequently, 15 ml of a 0.25-molar HCl solution and 30 ml Et2O were added, and the mixture obtained was vigorously stirred for 10 minutes. The phases were separated, the organic components were extracted twice from the aqueous phase with 15 ml Et2O each, the combined organic phases were washed with 10 ml brine, then dried and concentrated under reduced pressure. The raw product obtained was cleaned by means of a silica column with 5% diethyl ether/light gasoline. The ketone was obtained as a colorless oil.

Provenance & Evidence