Cornforth reagent → 3-Hydroxy-5-oxo-4a,5,6,7,8,8a-hexahydro-naphthalene-2-carboxylic acid methyl ester

Participants

Reaction Steps

To a solution of 3,5-Dihydroxy-4a,5,6,7,8,8a-hexahydro-naphthalene-2-carboxylic acid methyl ester (3 g, 13.5 mmol) in DCM (100 mL) is added PDC (5.33 g, 14.2 mmol). The suspension is stirred at room temperature overnight. Upon completion of the reaction, the mixture is filtered through a short silica gel pad rinsing with DCM. After evaporation of the solvent, the crude product is obtained as light yellow solid. Recrystallization with DCM and hexanes affords 2.4 g of 3-hydroxy-5-oxo-4a,5,6,7,8,8a-hexahydro-naphthalene-2-carboxylic acid methyl ester as white crystalline solid; LC/MS calculated for [M+H]+ C12H12O4: 221.1, found: 221.1.

Provenance & Evidence