I[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:13]([Mg]Cl)([CH3:15])[CH3:14].C(Br)C=C.C([Cu])#N>C1COCC1>[CH2:8]([O:7][C:5](=[O:6])[C:4]1[CH:10]=[CH:11][CH:12]=[C:2]([CH2:15][CH:13]=[CH2:14])[CH:3]=1)[CH3:9]A −45° C. solution of ethyl 3-iodobenzoate (2.434 g, 8.8 mmol) in 40 mL THF was treated with i-PrMgCl (4.8 mL, 9.6 mmol, 2 M/ether). After 1 h, allyl bromide (1.6 mL, 18.9 mmol) was added followed by CuCN (79 mg, 0.88 mmol). The reaction was stirred for 1 h and then was quenched by addition of 50 mL saturated NH4Cl solution. Water (30 mL) was added and the resulting mixture was extracted with ethyl acetate (3×50 mL). The combined ethyl acetate solution was dried (MgSO4), filtered and evaporated. Purification by flash chromatography on silica gel (5% ethyl acetate/hexanes→10%) gave compound 7 (1.145 g, 68%).
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