Potassium sodium tartarate → (2-Isopropyl-4-methyl-1,3-thiazol-5-yl)methanol

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Reaction Steps

Diisobutylaluminum hydride (1.5M in toluene; 6.5 mL, 9.8 mmol) was added dropwise to a solution of 2-(1-methylethyl)-4-methylthiazole-5-carboxylic acid ethyl ester (Example 9; 1.0 g, 4.7 mmol) in toluene (8 mL) at −75° C. After 15 min, the cold reaction mixture was treated with saturated aqueous potassium sodium tartrate (15 mL) and the reaction mixture was allowed to warm to room temperature. The reaction mixture was filtered and the solids were washed thoroughly with toluene. The combined filtrates were washed with brine (50 mL) and the brine layer was back-washed with toluene (3×35 mL) and ethyl acetate (2×35 mL) to extract the product completely. The combined organic layers were dried (MgSO4), filtered and evaporated under reduced pressure to give 2-(1-methylethyl)-4-methylthiazole-5-methanol (742 mg, 92% yield).

Provenance & Evidence