Tetrabutylammonium Fluoride → HCID 71087311, compound

HRID 242375Notes

Reaction equation

HRID 242375 reaction equation
[CH3:1][N:2]([CH3:33])[S:3]([N:6]1[CH:10]=[C:9]([CH2:11][O:12][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[N:8]=[C:7]1[C:30](=[O:32])[CH3:31])(=[O:5])=[O:4].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)(=O)C>[CH3:33][N:2]([CH3:1])[S:3]([N:6]1[CH:10]=[C:9]([CH2:11][OH:12])[N:8]=[C:7]1[C:30](=[O:32])[CH3:31])(=[O:4])=[O:5]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 71087512HCID 71087512, compound

Product 1

HCID 71087311HCID 71087311, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (0.910 g) obtained in (2) was dissolved in THF (10 mL), followed by addition of TBAF (1.0 M THF solution, 4.08 mL) under stirring, and the stirring was continued for 21 hours. The reaction solution was diluted with ethyl acetate, washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate to distill off the solvent under reduced pressure. The resulting residue was purified by flash chromatography (ethyl acetate/hexane=20%→100%) using amino column (product name: Hi-Flash Column 2 L, manufactured by Yamazen Corporation) to afford the title compound (0.170 g).

Workup

  1. washwashed with saturated brine
  2. dry with materialsubsequently dried over anhydrous magnesium sulfate
  3. distillationto distill off the solvent under reduced pressure
  4. customThe resulting residue was purified by flash chromatography (ethyl acetate/hexane=20%→100%)

Sources & evidence

ORD record
ord-e00f46915d1f4c85b4dc495387ed7f77
Source dataset
uspto-grants-2014_02
Patent number
US08653126B2

Reaction notes

Loading…