Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]C.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.[NH4+].[Cl-].Cl>C(OCC)C>[CH3:11][O:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:15]([CH:16]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH:14]=1To dry diethyl ether (50 mL) containing Mg turnings (1.22 g; 50 mmol) under N2 was added 1-bromononane (8.6 mL; 50 mmol) at a rate sufficient to maintain slow reflux. The reaction mixture was stirred for 45 minutes after the end of addition, cooled on an ice/water bath and 3-methoxy benzaldehyde (6.1 mL; 50 mmol) was then added drop wise. The reaction mixture was allowed to warm to room temperature overnight, added saturated aqueous NH4Cl (50 mL) and then 4 M HCl (aq.; 10 mL). The organic phase was isolated, dried (MgSO4), filtered and purified by column chromatography (SiO2; EtOAc/PE80-100° C.=1:10) to yield 7.4 g (64%) pure product.
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