Tetrabutylammonium Fluoride → 2-Ethynyl-5-(4-methoxyphenyl)pyrazine

HRID 76140Notes

Reaction equation

HRID 76140 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[N:13][C:12]([C:15]#[C:16][Si](C)(C)C)=[CH:11][N:10]=2)=[CH:5][CH:4]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C(Cl)Cl>[C:15]([C:12]1[CH:11]=[N:10][C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:14][N:13]=1)#[CH:16]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 666111672-(4-Methoxyphenyl)-5-((trimethylsilyl)ethynyl)pyrazine

Product 1

HCID 870851692-Ethynyl-5-(4-methoxyphenyl)pyrazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2.00 g (7.08 mmol) 2-(4-methoxyphenyl)-5-((trimethylsilyl)ethynyl)pyrazine in 50 mL DCM are added 2.08 g (7.44 mmol) TBAF*H2O and the reaction mixture is stirred at r.t. for 30 min. The mixture is washed with 50 mL water (3×) and the organic layer is dried with MgSO4 and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, PE/EtOAc 100/0→80/20).

Workup

  1. washThe mixture is washed with 50 mL water (3×)
  2. dry with materialthe organic layer is dried with MgSO4
  3. customthe solvent is removed in vacuo
  4. customThe crude product is purified by column chromatography (silica gel, PE/EtOAc 100/0→80/20)

Sources & evidence

ORD record
ord-3a9d6764fffd41d2b09dca3377d4193e
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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