[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:11][C:12]1[CH:25]=[CH:24][CH:23]=[CH:22][C:13]=1[O:14][C:15]1[S:19][C:18]([C:20]#[N:21])=[CH:17][CH:16]=1.N.S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1>[Cl:11][C:12]1[CH:25]=[CH:24][CH:23]=[CH:22][C:13]=1[O:14][C:15]1[S:19][C:18]([CH2:20][NH2:21])=[CH:17][CH:16]=1To a solution of lithium aluminum hydride (1.79 g, 47.1 mmol) in tetrahydrofuran was added aluminum chloride (7.54 g, 56.5 mmol) on an ice bath, which was then stirred for 10 minutes. To the suspension was 5-(2-chloro-phenoxy)-thiophene-2-carbonitrile described in Preparation Example 158 (2.22 g, 9.42 mmol) was added on an ice bath, and the solution was stirred for 1 hour. An aqueous ammonia was added to the reaction solution, then, anhydrous magnesium sulfate was added for drying, and the solution was filtered through Celite pad. The filtrate was concentrated in vacuo, the residue was purified by NH silica gel column chromatography (heptane/ethyl acetate=1/2), and the title compound (2.26 g, 9.42 mmol, 100%) was obtained as a light brown oil.
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