Hydrochloric Acid → Methyl 2-[(6-chloro-1,2-benzisoxazol-3-yl)oxy]propionate

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Reaction Steps

A mixture of 6-chloro-1,2-benzisoxazol-3-ol (6.8 g, 40.1 mmol), potassium carbonate (8.3 g, 60 mmol) and methyl 2-bromopropionate (10.0 g, 60.1 mmol) in N,N-dimethylformamide is stirred at room temperature overnight and diluted with water. The resultant aqueous mixture is acidified with concentrated hydrochloric acid (pH5-pH6) and extracted with methylene chloride. The combined organic extracts are diluted with hexanes, washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a residue. Column chromatography of the residue using silica gel and ethyl acetate/hexanes solutions gives the title product as a gold oil which is identified by NMR spectral analyses.

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