BAY-i 9139 → 2-Acetoxy-1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethylbutane

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Reaction Steps

8.0 g (0.027 mol) of 1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethyl-butan-2-ol are heated in 40 ml of acetic anhydride with 0.15 g of sodium acetate for 10 hours at 100° C. The solution is then cooled and stirred into 400 ml of ice water, the temperature being kept at 20°-25° C. The mixture is left to stand overnight. A smeary crystalline mass precipitates out and is taken up in chloroform. The chloroform solution is washed several times with water and sodium bicarbonate solution, dried over sodium sulphate and concentrated in vacuo by distilling off the solvent. The crystalline residue is boiled up in petroleum ether and the product is filtered off cold and dried. 4.5 g (49% of theory) of 2-acetoxy-1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethyl-butane are obtained as a mixture of isomers with a melting point of 81°-91° C.

Provenance & Evidence