Boron trifluoride etherate → Ethyl 5-oxothiepane-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a cold solution (−30° C.) of tetrahydrothiopyran-4-one (5.0 g, 43.0 mmol) in anhydrous ether, were simultaneously added a solution of boron trifluoride etherate (5.4 ml, 43.0 mmol) in diethyl ether (4.6 ml) and a solution of ethyl diazodicarboxylate (5.8 ml, 55.9 mmol) in diethyl ether (4.6 ml) over 1.5 hours via a syringe pump. Upon completion of additions, the reaction mixture was allowed to stir for an additional hour at −30° C. and then warmed to room temperature. The reaction mixture was washed with 30% potassium carbonate and the organic phase was dried over Na2SO4 and concentrated in vacuo to give ethyl 5-oxothiepane-4-carboxylate as a white solid.

Provenance & Evidence