Pyridinium chloride → 3-Thieno[2,3-d]isoxazol-3-yl-phenol

Participants

Reaction Steps

Eight grams of 3-(3-methoxyphenyl)thieno[2,3-d]isoxazole was stirred with 80 g of pyridine hydrochloride for nine hours under nitrogen at 140° C. The reaction mixture was then allowed to cool and quenched with water. The organics were extracted into ether/ethyl acetate (1:1), which was then washed once with 3N hydrochloric acid and three times with water an dried over anhydrous magnesium sulfate. Evaporation of the solvents left 4 g of an oil, which was passed through a silica gel column packed in hexane. Elution of the column with 5% ethyl acetate/dichloromethane and recrystallization of the resultant solid from ether/hexane gave 3 g of a solid, m.p. 114°-116° C.

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