Tetrabutylammonium Fluoride → 5-(4-Chloro-phenyl)-2-ethynyl-pyridine

HRID 734779Notes

Reaction equation

HRID 734779 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([C:26]#[C:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)=[CH:30][N:29]=1)(C(C)(C)C)(C)C>C(Cl)Cl>[Cl:40][C:37]1[CH:36]=[CH:35][C:34]([C:31]2[CH:32]=[CH:33][C:28]([C:27]#[CH:26])=[N:29][CH:30]=2)=[CH:39][CH:38]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 690583502-[(Tert-butyldimethylsilanyl)ethynyl]-5-(4-chlorophenyl)pyridine

Product 1

HCID 578453285-(4-Chloro-phenyl)-2-ethynyl-pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

43.66 g (156.0 mmol) of TBAF was added to a solution of 46.50 g (142.0 mmol) of 2-[(tert-butyldimethylsilanyl)ethynyl]-5-(4-chlorophenyl)pyridine in 1 L of DCM at RT and the mixture was stirred for 2 hours. The organic phase was washed with water, dried over sodium sulfate, and evaporated down in vacuo. The residue was stirred with DIPE, and the precipitate was filtered off and washed with PE. Yield: 26.0 g (86% of theoretical); C13H8ClN (M=213.662); calc.: molpeak (M+H)+: 214/216 (Cl); found: molpeak (M+H)+: 214/216 (Cl); Rf value: 0.30 (silica gel, cyc/EtOAc 4:1).

Workup

  1. washThe organic phase was washed with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated down in vacuo
  4. stirringThe residue was stirred with DIPE
  5. filtrationthe precipitate was filtered off
  6. washwashed with PE

Sources & evidence

ORD record
ord-c49bc3c416844058858140a2cd67f8ac
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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