Tetrabutylammonium Fluoride → HCID 85969792, compound

HRID 1916517Notes

Reaction equation

HRID 1916517 reaction equation
[CH2:1]([N:3]([CH2:19][CH3:20])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si](C)(C)C)=[CH:9][CH:8]=1)[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:19]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[CH:14])=[CH:11][CH:12]=1)[CH3:20]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 14572730HCID 14572730, compound

Product 1

HCID 85969792HCID 85969792, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere a solution of 1.4 g (4.8 mmol) diethyl-[2-(4-trimethylsilanylethynyl-phenoxy)-ethyl]-amine in 50 mL THF is combined with 1.68 g (5.3 mmol) TBAF and stirred overnight at RT. The solvent is distilled off i.vac., the residue is taken up in water, exhaustively extracted with EtOAc and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified on silica gel (EtOAc/MeOH 95:5).

Workup

  1. distillationThe solvent is distilled off i.vac
  2. extractionexhaustively extracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. customis purified on silica gel (EtOAc/MeOH 95:5)

Sources & evidence

ORD record
ord-3dc35beaae494824ab45ee87a7feaf9d
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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