Tetrabutylammonium Fluoride Trihydrate → HCID 66930678, compound

HRID 1510176Notes

Reaction equation

HRID 1510176 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:31][C@H:32]1[O:61][C@H:60]([CH2:62][O:63][CH2:64][C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[C@H:51]([O:52][CH2:53][C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[C@H:42]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C@H:33]1[O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C@H:10](O[Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)[CH:11]=[CH2:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH2:71].O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C([O-])(O)=O.[Na+]>[C:1]([O:5][C:6]([NH:8][C@@:9]([OH:71])([CH2:31][C@H:32]1[O:61][C@H:60]([CH2:62][O:63][CH2:64][C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[C@H:51]([O:52][CH2:53][C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[C@H:42]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C@H:33]1[O:34][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[CH2:10][CH:11]=[CH2:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 86650527HCID 86650527, compound

Product 1

HCID 66930678HCID 66930678, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To 12 (2.51 g, 2.56 mmol, 1 eq) dissolved in THF (11 mL) at room temperature was added tetrabutylammonium fluoride trihydrate (2.02 g, 6.41 mmol, 2.5 eq). The mixture was stirred at room temperature for 16 h and diluted with saturated aqueous NaHCO3 solution (30 mL). The aqueous layer was extracted with EtOAc (3×100 mL). The organic layers were combined, dried over MgSO4 and concentrated. Purification by flash chromatography on silica gel (petroleum ether/EtOAc 65:35) afforded 13 as white solid (1.6 g, 85%).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc (3×100 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customPurification by flash chromatography on silica gel (petroleum ether/EtOAc 65:35)

Sources & evidence

ORD record
ord-31d9f7e626a94acfa3c0396887912e71
Source dataset
uspto-grants-2012_07
Patent number
US08211859B2

Reaction notes

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