Tetrabutylammonium Fluoride → HCID 11121945, compound

HRID 244261Notes

Reaction equation

HRID 244261 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-506c5a086e9141dbbb51af21ef06d5c6
Source dataset
uspto-grants-2014_02
Patent number
USRE044779E1

Reaction notes

Loading…