[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[C:12]([C:13](OCC)=[O:14])=[C:11]([Cl:18])[N:10]([CH2:19][CH3:20])[N:9]=1.C(OCC)(=O)C.O>O1CCCC1>[Cl:7][C:8]1[C:12]([CH2:13][OH:14])=[C:11]([Cl:18])[N:10]([CH2:19][CH3:20])[N:9]=1A solution of 0.16 g (4.2 mmoles) of lithium aluminum hydride dissolved in 70 ml of tetrahydrofuran was cooled to −50° C. Thereto was gradually added dropwise a solution of 1.0 g (4.2 mmoles) of ethyl 3,5-dichloro-1-ethyl-1H-pyrazole-4-carboxylate dissolved in 30 ml of tetrahydrofuran. The mixture was stirred at −50° C. for 3 hours to give rise to a reaction. After confirmation of the completion of the reaction, ethyl acetate was added, followed by stirring for a while. Water was added, followed by stirring for a while. The resulting mixture was filtered under vacuum. The filtrate was extracted with ethyl acetate. The resulting organic layer was washed with water and an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein, to obtain 0.82 g (yield: 100%) of (3,5-dichloro-1-ethyl-1H-pyrazol-4-yl)methanol as a brown oily substance.
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