[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11].[CH:14]([Mg]Br)=[CH2:15].[Cl-].[NH4+]>C1COCC1>[OH:1][CH:2]([CH:14]=[CH2:15])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11]To a solution of methyl 9-oxononanate (260.4 mg) in THF (4 ml) was dropwise added 0.95M vinyl magnesium bromide (1.62 ml) at —70° C. and then stirred for 1 hour at −60° C. The reaction mixture was poured into a saturated ammonium chloride aqueous solution and then extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate anhydride, and then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to give methyl 9-hydroxy-10-undecenate (144 mg, 47.4%).
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