[CH3:1][O:2][CH:3]([O:9][CH3:10])[C:4]1[CH:8]=[CH:7][S:6][CH:5]=1.CCOCC.C([Li])CCC.[F:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH:24]=[O:25]>O1CCCC1>[CH3:1][O:2][CH:3]([O:9][CH3:10])[C:4]1[CH:8]=[CH:7][S:6][C:5]=1[CH:24]([C:23]1[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=1[F:21])[OH:25]To 3-thiophenecarboxaldehyde dimethyl acetal (11.9 g) and ether (180 ml) was added n-butyllithium (31.0 ml, 2.5M in hexanes) at a rate so as to maintain gentle reflux of the solvent. The mixture was heated under reflux for 0.5 hr, cooled to ambient temperature, diluted with tetrahydrofuran (50 ml), was cooled to -78° C., and 2-fluorobenzaldehyde (8.50 ml) in tetrahydrofuran (90 ml) was added. The reaction mixture was allowed to warm to ambient temperature over several hrs and was quenched with dilute aqueous ammonium chloride solution and ether. The layers were separated and the organic layer was washed with dilute aqueous ammonium chloride solution. The combined aqueous layers were back-extracted with ether, and the combined organic layers were washed with brine, dried over anhydrous potassium carbonate, and filtered. Concentration of the residue afforded 3-(dimethoxymethyl)-α-(2-fluorophenyl)-2-thiophenemethanol.
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