Tetrabutylammonium Fluoride → HCID 67085451, compound

HRID 1047464Notes

Reaction equation

HRID 1047464 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:24][CH:25]1[CH2:29][CH:28]([N:30]2[CH:38]=[N:37][C:36]3[C:31]2=[N:32][C:33]([NH2:40])=[N:34][C:35]=3[Cl:39])[C:27](=[CH2:41])[CH:26]1[CH2:42][O:43][C:44]([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)(C)(C)C>O1CCCC1>[NH2:40][C:33]1[N:34]=[C:35]([Cl:39])[CH:36]2[CH:31]([N:32]=1)[N:30]([CH:28]1[CH2:29][CH:25]([OH:24])[CH:26]([CH2:42][O:43][C:44]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:27]1=[CH2:41])[CH:38]=[N:37]2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 76035569HCID 76035569, compound

Product 1

HCID 67085451HCID 67085451, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1 M tetrabutyl ammonium fluoride solution in tetrahydrofuran (1.1 L, 1.10 mol) was added to a solution prepared by dissolving the compound of formula (V) obtained in Example 2-9 (426 g, 0.5487 mol) in anhydrous tetrahydrofuran (4 L) and stirred at room temperature for 13 hrs. After completion of the reaction, distilled water (2.0 L) was added to the resulting mixture and extracted with ethyl acetate (2.0 L) twice. The organic layer thus separated was dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting material was stirred in methanol (4.0 L) to obtain the title compound (212.6 g, yield: 72%).

Workup

  1. customprepared
  2. customAfter completion of the reaction
  3. distillationdistilled water (2.0 L)
  4. additionwas added to the resulting mixture
  5. extractionextracted with ethyl acetate (2.0 L) twice
  6. customThe organic layer thus separated
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. stirringThe resulting material was stirred in methanol (4.0 L)

Sources & evidence

ORD record
ord-93d2a6aaa8464d4db7f7955e4173388c
Source dataset
uspto-grants-2013_10
Patent number
US08569491B2

Reaction notes

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