[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]#[N:9])[CH2:4][CH2:3]1.[CH3:10]C(C)([O-])C.[K+].[I-].C[S+](C)(C)=O>CS(C)=O.[Cl-].[Na+].O>[O:1]1[C:2]2([CH2:7][CH2:6][CH:5]([C:8]#[N:9])[CH2:4][CH2:3]2)[CH2:10]1A solution of 4-oxocyclohexanecarbonitrile (1.90 g) in dimethylsulfoxide (8 mL) was added dropwise to a solution of potassium t-butoxide (2.60 g) and trimethylsulfoxonium iodide (5.09 g) in dimethylsulfoxide (30 mL) at room temperature. The mixture was stirred overnight, diluted with 20% brine, and extracted with 3× ethyl acetate. The combined organic layers were washed with 20% brine, dried over Na2SO4, and concentrated. The crude was purified on a 40 g column using an ISCO Companion flash system eluting with hexane/ethyl acetate (6:4 to 5:5) to give the desired product.
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