C[O:2][C:3]([C:5]1[CH:13]=[CH:12][C:8]2[N:9]=[CH:10][S:11][C:7]=2[CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[S:11]1[C:7]2[CH:6]=[C:5]([CH2:3][OH:2])[CH:13]=[CH:12][C:8]=2[N:9]=[CH:10]1Add slowly a solution of benzothiazole-6-carboxylic acid methyl ester (0.5 g, 2.59 mmol) in anhydrous THF (10 mL) to a suspension of lithium aluminum hydride (0.1 g, 2.85 mmol) in anhydrous THF (20 mL) at −10° C. and stir for 20 min at −10° C. Treat the reaction mixture with 2N aqueous NaOH until a granular precipitate starts to form and filter through a pad of Celite®. Evaporate the solvent and purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 4:1, 7:3, 3:2 and 1:1) to obtain the desired intermediate as a yellow oil (0.4 g, 99%). MS (ES+) m/z: 166 (M+H)+.
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