Hydrochloric Acid → HCID 13075145, compound

Participants

Reaction Conditions

Reaction Steps

To 9.4 g (0.052 mol) of benzenesulfonyl-acetonitrile in 200 mL of DME at −50° C., 7.8 mL (0.052 mol, 1 eq) of TMEDA and 32.4 mL (0.052 mL, 1 eq) of nBuLi (1.6M in hexane) were added and stirring was continued for 45 min. To the resulting white suspension, 4.98 g (0.052 mol, 1 eq) of cyclohex-2-enone were added and the temperature was raised to −10° C. within 4 hours. The reaction mixture was poured into 180 mL of 1M HCl, extracted with EtOAc, and the combined organic phases dried over Na2SO4. Evaporation of the solvent and recrystallisation from AcOEt/Et2O yielded 8.25 g (57%) of benzenesulfonyl-(3-oxo-cyclohexyl)-acetonitrile as a racemic mixture of diastereomers, white crystals, MS: 278 (MH+) (in analogy to: E. Hatzigrigoriou, L. Wartski, Synth. Comm., 1983, 14(4), 319-235).

Provenance & Evidence