Potassium Fluoride → HCID 15811458, compound

HRID 556141Notes

Reaction equation

HRID 556141 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][Si](C)(C)C)=[CH:15][N:14]=2)=[N:11][CH:12]=1)(C)C.[F-].[K+]>CO>[C:19]([C:16]1[CH:17]=[CH:18][C:13]([C:10]2[CH:9]=[CH:8][C:7]([C:6]#[CH:5])=[CH:12][N:11]=2)=[N:14][CH:15]=1)#[CH:20]

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 5247662HCID 5247662, compound

Product 1

HCID 15811458HCID 15811458, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Subsequently, the obtained 5,5′-bis(trimethylsilylethynyl)-2,2′-bipyridyl (120 mg, 0.34 mmol) and potassium fluoride (KF: 42 mg, 0.72 mmol) were added with dist. methanol (MeOH: 12 mL). The resultant mixture was then stirred under a nitrogen atmosphere at room temperature for 11 hours to obtain a reaction mixture. After that, an organic layer in the reaction mixture was then concentrated to obtain a crude product (II). Subsequently, the obtained crude product (II) was separated and purified by silica gel column chromatography (CH2Cl2=100) to obtain 5,5′-diethynyl-2,2′-bipyridyl (59.5 mg, 85% yield (in two steps)).

Workup

  1. customto obtain a reaction mixture
  2. concentrationAfter that, an organic layer in the reaction mixture was then concentrated
  3. customto obtain a crude product (II)
  4. customSubsequently, the obtained crude product (II)
  5. customwas separated
  6. custompurified by silica gel column chromatography (CH2Cl2=100)

Sources & evidence

ORD record
ord-d8eb6f44f47f480fb4c8db71a8ae96af
Source dataset
uspto-grants-2011_11
Patent number
US08053588B2

Reaction notes

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