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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%).

1. customwas quenched by addition of 50 mL saturated NH4Cl solution
2. additionWater (30 mL) was added
3. extractionthe resulting mixture was extracted with ethyl acetate (3×50 mL)
4. dry with materialThe combined ethyl acetate solution was dried (MgSO4)
5. filtrationfiltered
6. customevaporated
7. customPurification by flash chromatography on silica gel (5% ethyl acetate/hexanes→10%)