Trifluoromethanesulfonic anhydride → 1,4-Dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate

HRID 2046782Notes

Reaction equation

HRID 2046782 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[O:22](S(C(F)(F)F)(=O)=O)[S:23]([C:26]([F:29])([F:28])[F:27])(=O)=[O:24]>CCOCC>[F:27][C:26]([F:29])([F:28])[S:23]([O:11][C:8]1[CH2:7][CH2:6][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:10][CH:9]=1)(=[O:24])=[O:22]

Participants

5

Reactant 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 114830861,4-Dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonateYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-15 °C

Procedure

1,4-Dioxaspiro[4.5]decan-8-one (1.0 equiv) was dissolved in Ether (0.1 M) and stirred at −15° C. then 1M NaHMDS (1.05 equiv.) was added and stirred for 70 min then Tf2O (1.05 equiv.) added and reaction allowed to slowly warm to rt. The mixture was stirred for 28 hr, washed with sat. aq. NaHCO3 and then water. Aqueous layers combined and extracted with ether. Organic layers combined, dried over MgSO4, filtered, and concentrated. The residue was purified by column (ethyl ether:hexanes=1:4) to give 1,4-dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate (65%). LC/MS (m/z): MH+=289.0, Rt=0.97. HPLC Rt=3.77.

Workup

  1. stirringstirred for 70 min
  2. customreaction
  3. temperatureto slowly warm to rt
  4. stirringThe mixture was stirred for 28 hr
  5. washwashed with sat. aq. NaHCO3
  6. extractionextracted with ether
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by column (ethyl ether:hexanes=1:4)

Sources & evidence

ORD record
ord-9e92c3ffe4fa4071ba904f9fdb8cafad
Source dataset
uspto-grants-2013_11
Patent number
US08592455B2

Reaction notes

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