[C:1]1([CH3:22])[CH:6]=[CH:5][C:4]([C:7]2[S:11][C:10]([C:12]3C=CC=CC=3C(OC)=O)=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH2:29].[OH-].[Na+]>C1COCC1>[C:1]1([CH3:22])[CH:6]=[CH:5][C:4]([C:7]2[S:11][C:10]([CH2:12][OH:29])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1To a solution of methyl (5-p-tolylthiophen-2-yl)benzoate (5.0 mmol) in THF (20 mL) at 0° C. was slowly added LAH (1.0 M in THF, 6.0 mL). The reaction was then stirred at room temperature for 3 hours, and water (0.24 mL), 15% aqueous NaOH (0.24 mL), and water (0.72 mL) were added to the reaction mixture. After 30 minutes, the reaction mixture was filtered through celite and concentrated to give the pure product 13.1 (0.95 g). MS ESI (pos.) m/e 205.0 (M+H).
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