Tetrabutylammonium Fluoride → HCID 69809508, compound

HRID 1809463Notes

Reaction equation

HRID 1809463 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][C:28]1[C:29]2[C:33]([CH:34]=[CH:35][CH:36]=1)=[N:32][N:31]([C:37]1[CH:44]=[CH:43][C:40]([C:41]#[N:42])=[CH:39][CH:38]=1)[CH:30]=2)(C(C)(C)C)(C)C>C1COCC1.CCOC(C)=O>[OH:26][CH2:27][C:28]1[C:29]2[C:33]([CH:34]=[CH:35][CH:36]=1)=[N:32][N:31]([C:37]1[CH:38]=[CH:39][C:40]([C:41]#[N:42])=[CH:43][CH:44]=1)[CH:30]=2

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69812398HCID 69812398, compound

Product 1

HCID 69809508HCID 69809508, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

TBAF (1.3 eq., 1M in THF) was added dropwise to a solution of (C4) in dry THF (0.1 M) and allowed to stir at RT for 1 h. The reaction mixture was diluted with EtOAc and washed with 1N HCl (2×), sat. aq. NaHCO3, brine and dried (Na2SO4). Evaporation of the solvent yielded (100%) the title compound. 1H NMR (300 MHz, DMSO-d6, 300K) δ 9.33 (1H, s), 8.36 (2H, d, 8.5 Hz), 8.11 (2H, d, J=8.2 Hz*−), 7.62 (1H, d, J=8.5 Hz), 7.36 (1H, t, J=7.3 Hz), 7.12 (1H, d, J=6.6 Hz), 5.36 (1H, bt, J=5.4 Hz), 4.84 (2H, d, J=5.2 Hz). MS (ES+) C15H11N3O required: 249, found: 250 (M+H)+.

Workup

  1. washwashed with 1N HCl (2×), sat. aq. NaHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-5a24253e2fea440084f5828c43437cac
Source dataset
uspto-grants-2013_01
Patent number
US08362030B2

Reaction notes

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