Tetrahydrofuran → HCID 10386960, compound

HRID 2416182Notes

Reaction equation

HRID 2416182 reaction equation
C([Si](C)(C)[O:6][C:7]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]([S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH3:23])=[CH:18][CH:17]=1)([C:12]([F:15])([F:14])[F:13])[C:8]([F:11])([F:10])[F:9])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C[O:56]CC1>>[C:7]([OH:6])([C:12]([F:15])([F:14])[F:13])=[O:56].[F:11][C:8]([F:9])([F:10])[C:7]([C:16]1[CH:17]=[CH:18][C:19]([CH:22]([S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:25])=[O:26])[CH3:23])=[CH:20][CH:21]=1)([OH:6])[C:12]([F:15])([F:14])[F:13]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 86591358HCID 86591358, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 10386960HCID 10386960, compoundYield 86%

Conditions

Temperature
0 °C

Procedure

The product from step 2 (120 mg, 0.23 mmol) was dissolved in anhydrous THF (2 mL) under argon and cooled to 0° C. 1 M tetrabutylammonium fluoride solution in THF (0.5 mL, 0.5 mmol) was added and the reaction stirred for 30 min. The reaction was quenched at 0° C. with saturated NH4Cl and diluted with ethyl acetate. The layers were separated and the organic phase was washed with brine, dried (MgSO4), and concentrated in vacuo. Purification by reverse phase HPLC using a gradient elution of 60:40H2O/TFA:CH3CN to 0:100H2O/TFA:CH3CN at 254 nm afforded the title compound as a white solid (81 mg, 86%): mp=136° C. 1H NMR (CDCl3) δ 7.48-7.41 (m, 3H), 7.37 (d, 2H), 7.24 (m, 2H), 7.08 (d, 2H), 1H), 3.40 (br s, 1H), 1.67 (d, 3H). MS (ES+) m/z 430 (M+NH4+). Anal. Calc. for C17H14SO3F6: C, 49.52; H, 3.42. Found: C, 49.55; H, 3.28.

Workup

  1. customThe reaction was quenched at 0° C. with saturated NH4Cl
  2. additiondiluted with ethyl acetate
  3. customThe layers were separated
  4. washthe organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customPurification by reverse phase HPLC
  8. washa gradient elution of 60:40H2O/TFA

Sources & evidence

ORD record
ord-711bc1c76494496d8eff52cb29e84d60
Source dataset
uspto-grants-2004_11
Patent number
US06822120B2

Reaction notes

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