Tetrabutylammonium Fluoride → HCID 22174468, compound

HRID 1797334Notes

Reaction equation

HRID 1797334 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][O:16][Si](C(C)C)(C(C)C)C(C)C)[CH:5]=[CH:4][C:3]=1[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH3:35])=[O:28].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][OH:16])[CH:5]=[CH:4][C:3]=1[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH3:35])=[O:28]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22174477HCID 22174477, compound

Product 1

HCID 22174468HCID 22174468, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 441 (3.21 g, 6.32 mmol) and TBAF.3H2O (2.99 g, 6.32 mmol) were dissolved in THF (20 ml). The obtained reaction solution was stirred at RT for 0.5 h. After reaction the solution was concentrated in vacuo. The residue was redissolved in CH2Cl2 and washed with H2O. The aqueous phase was extracted twice with CH2Cl2. The combined organic phases were dried over MgSO4 and concentrated in vacuo. The crude product was purified by chromatography (petroleum ether/ethyl acetate 2:1) to give the title compound as reddish foam.

Workup

  1. customThe obtained reaction solution
  2. customAfter reaction the solution
  3. concentrationwas concentrated in vacuo
  4. dissolutionThe residue was redissolved in CH2Cl2
  5. washwashed with H2O
  6. extractionThe aqueous phase was extracted twice with CH2Cl2
  7. dry with materialThe combined organic phases were dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by chromatography (petroleum ether/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-4feaae3751104a5aac504d35946c8782
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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