1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-Hydroxy-6-methoxy-2-naphthalenecarboxylic acid, methyl ester

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Reaction Steps

A solution of 10.2 g (0.033 mole) of 1,2,3,4-tetrahydro-2-bromo-6-methoxy-1-oxo-2-naphthalenecarboxylic acid, methyl ester in 100 ml of tetrahydrofuran under a nitrogen atmosphere was treated over 15 minutes with a solution of 10.0 ml (10.2 g; 0.067 mole) of 1,8-diazabicyclo[5.4.0]undec-7-ene in 20 ml of tetrahydrofuran. The mixture was stirred at room temperature for 16 hours, then added to 450 g of ice/water. Acidification with 6.0N hydrochloric acid precipitated the crude naphthalene ester product. The solid was filtered, washed with water, and recrystallized from aqueous methanol to yield 5.1 g (67% yield) of the final product, mp 109°-111°. This material was identical with that prepared by the procedure described in Example 11.

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