Water → 5-(4-Chloro-phenyl)-2-ethynyl-pyridine

HRID 1916548Notes

Reaction equation

HRID 1916548 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[CH:28][C:29]([C:32]#[C:33][Si](C)(C)C)=[N:30][CH:31]=2)=[CH:22][CH:21]=1.O>C(Cl)Cl>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:27]=[CH:28][C:29]([C:32]#[CH:33])=[N:30][CH:31]=2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 673636115-(4-Chlorophenyl)-2-trimethylsilanylethynylpyridine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an argon atmosphere 6.6 g (21.0 mmol) TBAF are added to a solution of 5.8 g (20.3 mmol) 5-(4-chloro-phenyl)-2-trimethylsilanylethynyl-pyridine in 200 mL DCM at 0° C. The reaction solution is stirred for 3 h, while the reaction temperature slowly rises to RT. It is added to 50 mL water and the organic phase is extracted four times with 50 mL water, dried over MgSO4 and filtered over activated charcoal. The solvent is eliminated i.vac. and further purification is carried out by column chromatography on silica gel (PE/EtOAc 1:1).

Workup

  1. customslowly rises to RT
  2. extractionthe organic phase is extracted four times with 50 mL water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered over activated charcoal
  5. customand further purification

Sources & evidence

ORD record
ord-d186bbf9df2649b3aa1304bec28c4c7a
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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