Sodium Carbonate → 3-Oxocyclohex-1-en-1-yl trifluoromethanesulfonate
Reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.C([O-])([O-])=O.[Na+].[Na+].[O:15](S(C(F)(F)F)(=O)=O)[S:16]([C:19]([F:22])([F:21])[F:20])(=O)=[O:17]>C(Cl)Cl>[F:20][C:19]([F:22])([F:21])[S:16]([O:7][C:3]1[CH2:4][CH2:5][CH2:6][C:1](=[O:8])[CH:2]=1)(=[O:17])=[O:15]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of cyclohexane-1,3-dione (1 equiv) in DCM (0.4M) was added Na2CO3 (1.0 equiv.) and cooled to 0° C. Added Tf2O (1.0 equiv.) in DCM (5M) 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 purified via SiO2 column chromatography eluting with DCM and hexanes (1:1) or alternatively via a neutral alumina plug eluting with DCM to afford 3-oxocyclohex-1-enyl trifluoromethanesulfonate in 30% or 67% yield respectively. 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.
Workup
- additionUpon addition
- filtrationThe solution was filtered and to the filtrate
- additionwas added saturated NaHCO3 (carefully),
- extractionthen extracted the organics,
- dry with materialdried with brine
- concentrationNa2SO4, and concentrated
- customThe crude was purified via SiO2 column chromatography
- washeluting with DCM and hexanes (1:1) or alternatively via a neutral alumina plug
- washeluting with DCM
Sources & evidence
- ORD record
- ord-80da285fed944c14bfc791824e0e8928
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08829193B2
Reaction notes
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