[CH:1]1([C:4]2[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.C([Li])CCC.CCCCCC.[CH:22]([C:24]1[CH:29]=[CH:28][N:27]=[CH:26][C:25]=1[O:30][CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])=[O:23].[Cl-].[NH4+]>O1CCCC1>[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([CH:22]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][C:25]=3[O:30][CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[OH:23])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1To a solution of 4-cyclopropylbromobenzene (synthesized as described in WO0268439; 2.5 g, 0.0127 mol) in tetrahydrofuran (20 ml), a 1.58 mol/L n-butyllithium/n-hexane solution (8.4 ml, 0.0133 mol) was added dropwise at −70° C. over 8 minutes. After stirring at −70° C. for 1 hour, a tetrahydrofuran solution of 4-formyl-3-[2-(trimethylsilyl)ethoxymethoxy]pyridine (4.2 g, 0.0165 mol) was added over 5 minutes and stirred at −70° C. for 2.5 hours. After addition of saturated aqueous ammonium chloride, the reaction mixture was warmed to room temperature and extracted twice with ethyl acetate. The organic layers were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50) to give (4-cyclopropylphenyl)-[3-[2-(trimethylsilyl)ethoxymethoxy]pyridin-4-yl]-methanol (2.5 g, 53%) as a brown solid.
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