Perfluoro-1-butanesulfonyl fluoride → HCID 86629830, compound

HRID 456002Notes

Reaction equation

HRID 456002 reaction equation
[CH3:1][C:2]12[O:13][C:8]([CH3:14])([CH2:9][C:10](=[O:12])[CH2:11]1)[CH:7]1[CH:3]2[O:4][C:5]([CH3:16])([CH3:15])[O:6]1.C([N-]C(C)C)(C)C.[Li+].[F:25][C:26]([F:41])([C:37]([F:40])([F:39])[F:38])[C:27]([F:36])([F:35])[C:28]([F:34])([F:33])[S:29](F)(=[O:31])=[O:30]>C1COCC1.O>[CH3:14][C:8]12[O:13][C:2]([CH3:1])([CH:11]=[C:10]([O:12][S:29]([C:28]([F:33])([F:34])[C:27]([F:35])([F:36])[C:26]([F:25])([F:41])[C:37]([F:40])([F:39])[F:38])(=[O:31])=[O:30])[CH2:9]1)[CH:3]1[CH:7]2[O:6][C:5]([CH3:16])([CH3:15])[O:4]1

Participants

6

Reactant 3

HCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 2724682Lithium diisopropylamideHCID 68971583HCID 68971583, compound

Product 1

HCID 86629830HCID 86629830, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 1,4,4,7-tetramethyl-3,5,11-trioxa-tricyclo[5.3.1.02,6]undecan-9-one (Bulletin of the Chemical Society of Japan (1983), 56(9), 2680-99, 386 mg, 1.71 mmol) in THF (10 mL) was cooled to −78° C. under Ar and treated with lithium diisopropylamide (LDA) (1.00 mL of 2M in heptane/THF/ethylbenzene, 2 mmol). The resulting mixture was stirred at −78° C. for 2 h and treated dropwise with nonafluoro-1-butanesulfonylfluoride (0.60 mL, 3.4 mmol). The reaction mixture was allowed to warm to RT and stirred overnight and diluted with water (10 mL). The product was extracted with ether (4×10 mL). The organic layers were combined, dried (Na2SO4) and the product was purified on silica gel (0-2% EtOAc/hexane) to give the title compound (546 mg, 63%). 1H-NMR (CDCl3; 400 MHz): δ 5.78 (br s, 1H), 4.37 (d, 1H, J=5.5 Hz), 4.28 (d, 1H, J=5.5 Hz), 2.52 (dd, 1H, J=17.6, 2.0 Hz), 2.04 (d, 1H, J=17.6, 1.4 Hz), 1.43 (s, 3H), 1.38 (s, 3H), 1.32 (s, 3H), 1.25 (s, 3H).

Workup

  1. temperatureto warm to RT
  2. stirringstirred overnight
  3. extractionThe product was extracted with ether (4×10 mL)
  4. dry with materialdried (Na2SO4)
  5. customthe product was purified on silica gel (0-2% EtOAc/hexane)

Sources & evidence

ORD record
ord-4a72ebfefca540e0bf5ac047ba4a2699
Source dataset
uspto-grants-2013_07
Patent number
US08497376B2

Reaction notes

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