C1COCC1.[O:6]([C:13]1[S:17][C:16]([CH:18]=[O:19])=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O>[O:6]([C:13]1[S:17][C:16]([CH2:18][OH:19])=[CH:15][CH:14]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1To a solution of THF (60 mL) and 5-phenoxy-thiophene-2-carbaldehyde (2.8 g) was added LAH (390 mg) at 0° C., which was stirred for 10 minutes at room temperature. Water was added to the reaction solution, which was then extracted with ethyl acetate. The solvent was evaporated under a reduced pressure and the organic layer was purified by NH silica gel chromatography (ethyl acetate), and then purified by silica gel chromatography (hexane:ethyl acetate=4:1, then 2:1) to obtain the titled compound (2.0 g).
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