Imidazole → 2-Cyclopenten-1-ol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-

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Reaction Steps

To 1.592 g (15.9 mmol) of the oil, prepared as described in the preceding paragraph, was added successively 20 mL dimethylformamide, 1.51 g (22.3 mmol) imidazole, and 2.39 g (15.9 mmol) t-butyldimethylsilyl chloride. The resulting solution was stirred for 12 hrs, diluted with 100 mL of diethyl ether, and extracted 6 × (i.e., six times), each with 2 mL water. The organic phase was dried over MgSO4, filtered, and concentrated. Chromatography on a 2×18 cm column, packed with hexane and eluted with 100 mL each of 2%, 4%, 6%, 10%, 15%, and 20% ethyl acetate/hexane provided 683 mg clear colorless oil in 12 mL fractions 26-35.

Provenance & Evidence