CC[Mg+].[Br-].[C:5]1([CH3:13])[CH:10]=[CH:9][CH:8]=[C:7](C#N)[CH:6]=1.[CH:14]1[CH:19]=CC=C[CH:15]=1.Cl.CC[O:23]CC>>[CH3:15][CH2:14][CH2:19][C:13]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:23]To a 0° C. solution of EtMgBr in Et2O (3.0M, 570 mL, Aldrich) was slowly added m-tolunitrile (102 mL, Aldrich). After stirring at r.t. for 19 hr., benzene (300 mL) was added and the resulting mixture was cooled to 0° C. HCl (6N, 600 mL) was then slowly added. The organic phase was separated, washed with 5% NaHCO3 and brine, dried (MgSO4) and evaporated to afford the desired ketone as a yellow liquid.
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