Water → 2-but-3-ynyl-1-methyl-1H-benzoimidazole

HRID 1189141Notes

Reaction equation

HRID 1189141 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH3:19][N:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[C:21]1[CH2:29][CH2:30][C:31]#[C:32][Si](C)(C)C.O>C1COCC1>[CH2:29]([C:21]1[N:20]([CH3:19])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=1)[CH2:30][C:31]#[CH:32]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 66597967HCID 66597967, compound

Product 1

HCID 860868832-but-3-ynyl-1-methyl-1H-benzoimidazoleYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (0.24 mL, 0.83 mmol) was added to a solution of 1-methyl-2-(4-trimethylsilanyl-but-3-ynyl)-1H-benzoimidazole (178 mg, 0.69 mmol) in THF (2.5 mL) and the reaction mixture was stirred for 2 hours at room temperature. After the addition of water, the solvent was evaporated and the aqueous phase was extracted with DCM. The organic phase was washed with brine, dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1) to yield 90 mg (0.49 mmol, 70%) of 2-but-3-ynyl-1-methyl-1H-benzoimidazole as a brown solid.

Workup

  1. customthe solvent was evaporated
  2. extractionthe aqueous phase was extracted with DCM
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1)

Sources & evidence

ORD record
ord-580b91023bc748059436d124f36dfa45
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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