[CH:1]([Mg]Br)=[CH:2][CH2:3][CH3:4].[F:7][C:8]1[CH:9]=[CH:10][C:11]([O:18][CH3:19])=[C:12]([CH2:14][CH2:15][CH:16]=[O:17])[CH:13]=1.[Cl-].[NH4+]>C1COCC1>[CH3:19][O:18][C:11]1[CH:10]=[CH:9][C:8]([F:7])=[CH:13][C:12]=1[CH2:14][CH2:15][CH:16]([OH:17])[CH2:1][CH:2]=[CH:3][CH3:4]To a solution of 1-butenylmagnesium bromide (0.5 M in THF, 18 mL, 9.0 mmol) at 0° C. was added a solution of 3-(5′-fluoro-2′-methoxyphenyl)propionaldehyde (3.0 g, 16.5 mmol) in THF (30 mL) dropwise for 15 min. The reaction mixture was poured into a solution of saturated ammonium chloride (80 mL) in a separatory funnel. The organic function was extracted with ethyl acetate (3×80 mL) and the combined organic layers were washed with brine (80 mL) and dried over sodium sulfate. The solvent then was removed in vacuo and crude product thus obtained was purified by a flash column chromatography (15% EtOAc in hexane, Rf=0.20) to give the product as an oil (3.7 g, 94%).
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