Hydrogen Peroxide → (1R)-2-phenyl-1-(1,3-thiazol-2-yl)ethanol

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Reaction Conditions

Reaction Steps

Following the method of Itako et al. (Irako, N.; Hamada, Y.; Shioiri, T. Tetrahedron 48(35), 1992, 7251-7264), to a 0° C. (ice-water bath) solution of (+)-B -chlorodiisopinocamphenylborane (+-DIP-Chloride, 3.9 g, 12 mmol) in diethyl ether (3 mL) is added dropwise a solution of 2-phenyl-1-(1,3-thiazol-2-yl)ethanone (0.83 g, 4.1 mmol, from Reference Example 2) in diethyl ether (17 mL). The mixture is stirred for 6 hours at 0° C. and then is allowed to sit in a −5° C. freezer overnight. The next day, 10% aqueous sodium hydroxide solution (10 mL) is added at 0° C. with stirring. Aqueous hydrogen peroxide solution (30%, 1.5 mL) is then added and the mixture is allowed to stir at room temperature for 2 hours. The biphasic mixture is diluted with water (50 mL). The two layers are partitioned and the aqueous phase is saturated with potassium carbonate and then extracted thrice with diethyl ether. The combined extracts are washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a bright golden oil, which is purified by flash chromatography (silica gel, hexanes/ethyl acetate). A light yellow solid (0.60 g, 72%) is provided. MS (ES+): (M+H)=206.0

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