Tetrabutylammonium Fluoride → HCID 11995521, compound

HRID 2358309Notes

Reaction equation

HRID 2358309 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:36][CH2:37][CH:38]([NH:61][CH2:62][C:63]1[CH:64]=[N:65][CH:66]=[CH:67][CH:68]=1)[CH2:39][N:40]1[C:49]([C:50]#[N:51])=[C:48]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C:47]2[C:42](=[CH:43][CH:44]=[C:45]([O:58][CH3:59])[CH:46]=2)[C:41]1=[O:60])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[OH:36][CH2:37][CH:38]([NH:61][CH2:62][C:63]1[CH:64]=[N:65][CH:66]=[CH:67][CH:68]=1)[CH2:39][N:40]1[C:49]([C:50]#[N:51])=[C:48]([C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)[C:47]2[C:42](=[CH:43][CH:44]=[C:45]([O:58][CH3:59])[CH:46]=2)[C:41]1=[O:60]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58828515HCID 58828515, compound

Product 1

HCID 11995521HCID 11995521, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1M in THF, 0.15 mL, 0.15 mmol) was added to a solution of silyl ether 101 in THF (2.5 mL). After stirring for 2 h, the reaction mixture was partitioned between EtOAc and NaHCO3. The organic phase was washed once with brine and then dried (Na2SO4) and concentrated. The product was purified by automated flash chromatography (0-8% MeOH(NH3)/EtOAc).

Workup

  1. customthe reaction mixture was partitioned between EtOAc and NaHCO3
  2. washThe organic phase was washed once with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe product was purified by automated flash chromatography (0-8% MeOH(NH3)/EtOAc)

Sources & evidence

ORD record
ord-df43b756caa94dacb3a296f1bf1d0f47
Source dataset
uspto-grants-2010_07
Patent number
US07763614B2

Reaction notes

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