Acetic Acid → 3-Oxo-spiro[5.5]undecane-2-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of dimethyl carbonate (17.9 g) in tetrahydrofuran (130 mL) were added 60% sodium hydride (9.9 g) and potassium tert-butoxide (0.14 g). To the mixture was added a solution of spiro[5.5]undecan-3-one (20.6 g) obtained in the same manner as in Step 2 in tetrahydrofuran (120 mL) at 85° C. over 2 hours, followed by stirring the reaction mixture at 85° C. for 1.5 hours. After cooling down to room temperature and adding 15% aqueous acetic acid solution (94.2 mL), the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated to give 3-oxo-spiro[5.5]undecane-2-carboxylic acid methyl ester (29.6 g).

Provenance & Evidence