[CH:1]([Mg]Br)=[CH:2][CH2:3][CH3:4].[F:7][C:8]1[CH:9]=[CH:10][C:11]([O:17][CH3:18])=[C:12]([CH2:14][CH:15]=[O:16])[CH:13]=1.[Cl-].[NH4+]>C1COCC1>[CH3:18][O:17][C:11]1[CH:10]=[CH:9][C:8]([F:7])=[CH:13][C:12]=1[CH2:14][CH:15]([OH:16])[CH2:4][CH2:3][CH:2]=[CH2:1]To a solution of 1-butenylmagnesium bromide (0.5 M in THF, 9 mL, 4.5 mmol) at 0° C. was added a solution of 5-fluoro-2-methoxyphenylacetaldehyde (635 mg, 3.8 mmol) in THF (10 mL) dropwise for 15 min. Then the reaction mixture was poured in to a solution of saturated ammonium chloride (40 mL) in a separatory funnel. The organics were extracted with ethyl acetate (3×50 mL) and the combined organic layers were washed with brine (50 mL) and dried over sodium sulfate. The solvent was removed in vacuo and crude product thus obtained was purified by flash column chromatography (12.5% EtOAc in hexane, Rf=0.18) to give the product as an oil (642 mg, 74%).
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