Hexane → 2-(1,4,5-Trimethoxy-3-naphthylcarbonyl)-5-(2-methyl-dioxolan-2-yl)-6-oxa-bicyclo[3,2,1]octan-7-one

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Reaction Steps

7 ml of a 1.65 M hexane solution of n-butyllithium was dissolved in 30 ml of anhydrous tetrahydrofuran. To the solution was added at -78° C a solution of 3.3 g of 1,4,5-trimethoxy-3-bromo-naphthalene (VI, R=OCH3) in 30 ml of anhydrous tetrahydrofuran. 2,5 g of 2-methoxy-carbonyl-5-(2-methyl-dioxolan-2-yl)-6-oxa -bicyclo[3,2,1]-octan-7-one, prepared as described in Example 3, was dissolved in 50 ml of anhydrous tetrahydrofuran and added to the reaction mixture. The reaction mixture was stood for 1 hour at -78° C and then quenched with acetic acid. The solvent was removed in vacuo. The residue was purified by silica gel column chromatograhy, giving 3 g (73% yield) of the title compound. m/z 456 (M+.).

Provenance & Evidence