Hydrochloric Acid → HCID 136395593, compound

Participants

Reaction Steps

To a mixture consisting of 1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropanecarboxylic acid methyl ester (Example 1, Compound C, 7.16 g) in dioxane (120 mL) is added concentrated aqueous hydrochloric acid (30 mL.) The mixture is brought to 100° C. for three hours. The mixture is cooled and is poured into ice water. The mixture is treated with sodium bicarbonate and is extracted with ethyl acetate. The organic layer is dried over anhydrous sodium sulfate and is filtered and concentrated under reduced pressure. The concentrate is purified by flash silica gel column chromatography. Elution with hexanes-ethyl acetate (9:1 v/v) afforded the solid synthetic intermediate 1-[3-(4-hydroxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropanecarboxylic acid methyl ester (3.23 g, 9.63 mmol.)

Provenance & Evidence