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

HRID 2112813Notes

Reaction equation

HRID 2112813 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 are added at RT to a solution of 46.50 g (142.0 mmol) of 2-[(tert-butyldimethylsilanyl)ethynyl]-5-(4-chlorophenyl)pyridine in 1 L of DCM and the mixture is stirred for 2 hours. The organic phase is washed with water, dried over sodium sulfate, and evaporated down in vacuo. The residue is stirred with DIPE, and the precipitate is filtered off and washed with PE. Yield: 26.0 g (86% of theoretical);C13H8CIN (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 is washed with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated down in vacuo
  4. stirringThe residue is stirred with DIPE
  5. filtrationthe precipitate is filtered off
  6. washwashed with PE

Sources & evidence

ORD record
ord-3af0d899e53446aeac51803ff0b74290
Source dataset
uspto-grants-2009_04
Patent number
US07524862B2

Reaction notes

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