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

HRID 2192541Notes

Reaction equation

HRID 2192541 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

5

Reactant 3

HCID 10340Sodium CarbonateHCID 104341,3-CyclohexanedioneHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 109008513-Oxocyclohex-1-en-1-yl trifluoromethanesulfonateYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

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.

Workup

  1. additionUpon addition
  2. filtrationThe solution was filtered and to the filtrate
  3. additionwas added saturated NaHCO3 (carefully),
  4. extractionthen extracted the organics,
  5. dry with materialdried with brine
  6. concentrationNa2SO4, and concentrated
  7. customThe crude was used for the next step without further purification

Sources & evidence

ORD record
ord-6e781f0029664cb2bf1013a061a9fce6
Source dataset
uspto-grants-2012_12
Patent number
US08329732B2

Reaction notes

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