C([Li])CCC.[CH3:6][O:7][CH:8]([O:23][CH3:24])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[C:10]=1[O:19][CH2:20][O:21][CH3:22].CN(C)CCN(C)C.CN(C)[CH:35]=[O:36].Cl>C(OCC)C>[CH3:6][O:7][CH:8]([O:23][CH3:24])[C:9]1[C:10]([O:19][CH2:20][O:21][CH3:22])=[C:11]([C:15]([F:17])([F:18])[F:16])[CH:12]=[CH:13][C:14]=1[CH:35]=[O:36]A n-butyl lithium-1.59M n-hexane solution (196 ml, 312 mmol) was added dropwise to a solution of 1-(dimethoxymethyl)-2-(methoxymethoxy)-3-(trifluoromethyl)benzene (39.3 g, 140 mmol) obtained in Example (6-4) and N,N,N′,N′-tetramethylethylenediamine (46.9 ml, 311 mmol) in diethyl ether (410 ml) at −25° C. over 20 minutes. After the reaction mixture was stirred at 0° C. for 30 minutes, it was further stirred at room temperature for 1.5 hours. After the reaction mixture was cooled to −30° C. and N,N-dimethylformamide (41.9 ml, 541 mmol) was added thereto, the mixture was further stirred at room temperature for 1 hour. After the reaction mixture was carefully poured into cold 0.1N hydrochloric acid and the mixture was extracted with ethyl acetate (four times), the organic layer was successively washed with 0.1N hydrochloric acid, water (three times) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to give crude 2-(dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)benzaldehyde. This compound was used in Example (6-6) without further purification.
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