Hydrochloric Acid → HCID 59442682, compound

Participants

Reaction Conditions

Reaction Steps

5.10 g of 4-bromothioanisole were dissolved in 50 ml of dry THF and 9.29 ml of an n-butyllithium solution (2.7 M in HEP) were added dropwise at a temperature between −65° C. and −70° C. The reaction mixture was stirred for 3 h at −70° C. Subsequently a solution of 5.00 g of 4-oxo-1-phenylcyclohexanecarbonitrile in 30 ml of THF was added dropwise at this temperature and the mixture was stirred for 10 min at −70° C. and 26 h at room temperature. The reaction mixture was then poured onto 400 g of ice, 100 ml of a 1 N hydrochloric acid were added and the mixture was extracted three times with 200 ml each of DCM. The combined extracts were dried over magnesium sulfate and the solvent was removed in vacuo. Chromatography of the residue on silica gel with EA/HEP (1:2) yielded 5.96 g of the title compound as a colorless oil.

Provenance & Evidence