Trifluoromethanesulfonic anhydride → 3-Oxo-5-(trifluoromethyl)cyclohex-1-enyl trifluoromethanesulfonate

HRID 1523452Notes

Reaction equation

[F:1][C:2]([F:12])([F:11])[CH:3]1[CH2:8][C:7](=[O:9])[CH2:6][C:5](=[O:10])[CH2:4]1.[O:13](S(C(F)(F)F)(=O)=O)[S:14]([C:17]([F:20])([F:19])[F:18])(=O)=[O:15]>C(Cl)Cl>[F:18][C:17]([F:20])([F:19])[S:14]([O:9][C:7]1[CH2:8][CH:3]([C:2]([F:11])([F:12])[F:1])[CH2:4][C:5](=[O:10])[CH:6]=1)(=[O:15])=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 5-(trifluoromethyl)cyclohexane-1,3-dione (1.0 eq) in DCM (0.23 M) was added TEA (1.2 eq) to give a clear solution. The mixture was cooled to 0° C. And then Tf2O (1.05 eq) in DCM was added dropwise. The reaction mixture was stirred at that temperature for 2 hours. The reaction mixture was diluted with DCM, and washed with water, aq. NaHCO3, brine, and was dried over MgSO4, filtered and concentrated to give 3-oxo-5-(trifluoromethyl)cyclohex-1-enyl trifluoromethanesulfonate, which was used to next step directly. LC/MS (m/z): MH+=313.0, Rt=1.02 min.

Workup

customto give a clear solution
washwashed with water, aq. NaHCO3, brine
dry with materialwas dried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-a2e8e747750a4c6b93cfbdbe6bfb1e39
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079889B2

Reaction notes

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