Hydrochloric Acid → (3-Chloro-4-methylthiophen-2-yl)methanol
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[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[C:12]([CH3:13])=[CH:11][S:10][C:9]=1[C:14](OC)=[O:15].Cl>C1COCC1>[Cl:7][C:8]1[C:12]([CH3:13])=[CH:11][S:10][C:9]=1[CH2:14][OH:15][H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[C:12]([CH3:13])=[CH:11][S:10][C:9]=1[C:14](OC)=[O:15].Cl>C1COCC1>[Cl:7][C:8]1[C:12]([CH3:13])=[CH:11][S:10][C:9]=1[CH2:14][OH:15]Lithium aluminum hydride (1.35 g) was added to a THF (50 ml) solution of methyl 3-chloro-4-methylthiophene-2-carboxylate (3.40 g) at 0° C., followed by stirring at 0° C. for 20 minutes. An 1M aqueous hydrochloric acid solution was added to the reaction solution and the whole was stirred at room temperature for 1 hour. The solution was filtered and, after ethyl acetate was added, the organic layer was separated. Furthermore, the organic layer washed with brine and, after drying over anhydrous sodium sulfate and filtration, the solvent was removed by evaporation under reduced pressure. The resulting crude product was purified by column chromatography (hexane:ethyl acetate=4:1) to obtain 2.68 g of (3-chloro-4-methyl-2-thienyl)methanol (pale yellow oil).
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