Methanol → 7,8-dihydro-6,6-dimethyl-6H-[1,2,5]oxadiazolo[3,4-g][1,4]benzoxazine

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Reaction Steps

A mixture of 1.22 g 8-acetyl-7,8dihydro-6,6-dimethyl-6H-[1,2,5]oxadiazolo[3,4-g][1,4]benzoxazine, 40 ml methanol, 4 ml water and 1.37 g potassium carbonate was stirred at room temperature for one hour, the reaction mixture was poured into 300 ml ice water, and the resulting mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, the solvents were distilled off from the dried solution, and the residue was subjected to column chromatography on silica gel. Elution was conducted by the use of a 2:1 mixture of hexane and ethyl acetate, giving 1.02 g of 7,8-dihydro-6,6-dimethyl-6H-[1,2,5]oxadiazolo[3,4-g][1,4]benzoxazine.

Provenance & Evidence