[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1[S:8][N:9]=[C:10]2[CH:15]=[C:14]([C:16](OC)=[O:17])[CH:13]=[CH:12][C:11]=12.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C(OCC)C.C(OCC)(=O)C>[N:7]1[S:8][N:9]=[C:10]2[CH:15]=[C:14]([CH2:16][OH:17])[CH:13]=[CH:12][C:11]=12
To a suspension of lithium aluminum hydride (215 mg, 5.7 mmol) in diethyl ether (15 mL) at 0° C. was added methyl 2,1,3-benzothiadiazole-5-carboxylate (1.0 g, 5.2 mmol) in one portion. The reaction mixture was allowed to stir at 0° C. for 10 min, then at room temperature for 24 h. Ethyl acetate (30 mL) was added very slowly dropwise at 0° C. The reaction mixture was then added slowly to an aqueous solution of potassium sodium tartrate (30% w/v; 100 mL) and stirred for 2 h. The reaction mixture was diluted with 100 mL of ethyl acetate and the layers were separated. The aqueous layer was re-extracted with ethyl acetate (1×100 mL). The combined organic layers were dried (MgSO4), filtered and evaporated under reduced pressure. The crude product was purified by flash chromatography (silica gel, 25% ethyl acetate in petroleum ether) to give 2,1,3-benzothiadiazole-5-methanol (400 mg, 47% yield) as an orange solid.
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