[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[CH:10]([OH:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:23]I>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[CH:10]([O:15][CH3:23])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1The I'-A isomer (2 g) of 1-p-chlorophenyl-4,4-dimethyl-2-(1,2,4-triazole-1-yl)-1-pentene-3-ol (Compound No. 1) was dissolved in dimethylformamide (20 cc), and 65% oily sodium hydride (0.26 g) was added thereto. After stirring for 1 hour at room temperature, the reaction mixture was cooled to 10° C., and methyl iodide (1 g) was added. After standing at room temperature for 20 hours, the solvent was removed under reduced pressure, and the residue obtained was extracted with addition of ice water (100 g) and chloroform (100 cc). The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The oily crude product obtained was purified by column chromatography on silica gel (acetone:n-hexane=1:10) and further recrystallized from a carbon tetrachloride/n-hexane (1:2) mixture to obtain 1.6 g of the entitled compound (m.p. 63°-66° C.).
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