Tetrabutylammonium Fluoride → HCID 71087580, compound

HRID 242385Notes

Reaction equation

HRID 242385 reaction equation
[Si]([O:18][CH2:19][C:20]1[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:23]([C:33](=[O:35])[CH3:34])=[N:22][C:21]=1[CH3:36])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O>[OH:18][CH2:19][C:20]1[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:32])[CH3:31])[C:23]([C:33](=[O:35])[CH3:34])=[N:22][C:21]=1[CH3:36]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 71087571HCID 71087571, compound

Product 1

HCID 71087580HCID 71087580, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound (1.85 g) obtained in (3) was dissolved in THF (20 mL), followed by addition of TBAF (1.0 M THF solution, 3.54 mL) under stirring, and the stirring was continued for 1 hour. The reaction solution was diluted with water, followed by extraction with ethyl acetate. The combined extract was washed with saturated brine, dried over anhydrous sodium sulfate, and subsequently the solvent was distilled off under reduced pressure. The resulting residue was purified by flash chromatography (ethyl acetate/hexane=5%→70%) using amino column (product name: SNAP Cartridge NH 55 g, manufactured by Biotage, Ltd.) to afford the title compound (1.01 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. extractionThe combined extract
  3. washwas washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationsubsequently the solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by flash chromatography (ethyl acetate/hexane=5%→70%)

Sources & evidence

ORD record
ord-cee686f40c7e4518a3fb481b0532adff
Source dataset
uspto-grants-2014_02
Patent number
US08653126B2

Reaction notes

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