Sodium Carbonate → 3-Oxocyclohex-1-en-1-yl trifluoromethanesulfonate

Participants

Reaction Conditions

Reaction Steps

To a solution of cyclohexane-1,3-dione (1 equiv) in DCM (0.4 M) was added Na2CO3 (1.0 equiv.) and cooled to 0° C. Added Tf2O (1.0 equiv.) in DCM (5 M) dropwise over 1 hr at room temperature under a nitrogen atmosphere. Upon addition, the reaction was stirred for 2 hr (dark red solution). The solution was filtered and to the filtrate was added saturated NaHCO3 (carefully), then extracted the organics, dried with brine, then Na2SO4, and concentrated. The crude was used for the next step without further purification. 3-oxocyclohex-1-enyl trifluoromethanesulfonate was obtained in 67% yield. The triflate decomposes upon storage and should be used immediately for the next reaction. LC/MS=244.9/286.0 (M+H and M+CH3CN); Rt=0.88 min.

Provenance & Evidence