FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:17])[CH2:12][CH2:13][O:14]2)=[CH:9][CH:8]=1)(=O)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C-:39]#[N:40].[K+]>CC#N.Cl.O.CC(C)=O.CCOCC.[Zn]>[C:39]([C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:17])[CH2:12][CH2:13][O:14]2)=[CH:9][CH:8]=1)#[N:40]7-[[(Trifluoromethyl)sulfonyl]oxy]-4-chromanone (27.8 g, 94 mmol) and PPh3 (2.5 g, 9.6 mmol) were dissolved in degassed CH3CN (350 mL). KCN (6.8 g, 105 mmol), (PPh3)2NiBr2 (3.5 g, 4.7 mmol) and acid washed (stirred in 0.5 N HCl 1 min, washed successively with H2O, acetone, and Et2O) zinc dust (2.0 g, 31 mmol) were added and the reaction was purged with N2. The reaction was heated in a 60° C. bath for 6 h. The reaction was cooled, poured into H2O (400 mL) and extracted with EtOAc (3×300 mL). The organic layers were combined and washed with H2O (200 mL) and brine (150 mL). The solution was dried over MgSO4, filtered and concentrated in vacuo to provide a residue which was purified on a plug of silica (CH2Cl2 eluant) to provide the title compound.
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