Tetrabutylammonium Fluoride → HCID 11121945, compound

HRID 1387730Notes

Reaction equation

HRID 1387730 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([O:26][C@@H:27]1[C@@:31]2([CH2:51][O:52][C@H:28]1[C@H:29]([N:53]1[CH:60]=[C:59]([CH3:61])[C:57](=[O:58])[NH:56][C:54]1=[O:55])[O:30]2)[CH2:32][O:33][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[CH2:19]([O:26][C@@H:27]1[C@@:31]2([CH2:51][O:52][C@H:28]1[C@H:29]([N:53]1[CH:60]=[C:59]([CH3:61])[C:57](=[O:58])[NH:56][C:54]1=[O:55])[O:30]2)[CH2:32][OH:33])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 20675274HCID 20675274, compound

Product 1

HCID 11121945HCID 11121945, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen, tetrabutylammonium fluoride (1.0 M in THF, 379 μl, 0.379 μmol) was added to a tetrahydrofuran solution (1 ml) of Compound 37 (188.7 mg, 0.316 mmol), and the mixture was stirred for 2.5 hours at room temperature. The reaction mixture was distilled under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (AcOEt-hexane, 1:1→1:0) to obtain a white powder, Compound 38 (94.6 mg, 0.262 mmol, 83%).

Workup

  1. distillationThe reaction mixture was distilled under reduced pressure
  2. customthe resulting crude product was purified by silica gel column chromatography (AcOEt-hexane, 1:1→1:0)

Sources & evidence

ORD record
ord-69e64a4c221d45569a8380cc5aaa1dda
Source dataset
uspto-grants-2001_07
Patent number
US06268490B1

Reaction notes

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