[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[S:16][C:15]([CH2:17][CH3:18])=[N:14][C:13]=1[CH3:19])=O)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C(OCC)C>[CH2:17]([C:15]1[S:16][C:12]([CH2:10][OH:9])=[C:13]([CH3:19])[N:14]=1)[CH3:18]Lithium aluminum hydride (800 mg, 21.2 mmol) was added to a solution of 2-ethyl-4-methylthiazole-5-carboxylic acid ethyl ester (Example 11; 1.63 g, 8.2 mmol) in diethyl ether (100 mL). The solution was allowed to stir at room temperature for 4 h and was then poured carefully into an aqueous potassium sodium tartrate solution (30% w/v; 200 mL). After the mixture was allowed to stir at room temperature for 1 h, the layers were separated and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layers were washed with brine (200 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give 2-ethyl-4-methylthiazole-5-methanol (860 mg, 67% yield) as a colorless oil.
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