Tetrabutylammonium Fluoride → 2-(5-ethynyl-1-methyl-1H-imidazol-2-yl)-propan-2-ol

HRID 1350698Notes

Reaction equation

HRID 1350698 reaction equation
[CH3:1][N:2]1[C:6]([C:7]#[C:8][Si](C)(C)C)=[CH:5][N:4]=[C:3]1[C:13]([OH:16])([CH3:15])[CH3:14].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O>[C:7]([C:6]1[N:2]([CH3:1])[C:3]([C:13]([OH:16])([CH3:14])[CH3:15])=[N:4][CH:5]=1)#[CH:8]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 210972522-(1-Methyl-5-trimethylsilanylethynyl-1H-imidazol-2-yl)-propan-2-ol

Product 1

HCID 210972612-(5-ethynyl-1-methyl-1H-imidazol-2-yl)-propan-2-olYield 84.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 2-(1-Methyl-5-trimethylsilanylethynyl-1H-imidazol-2-yl)-propan-2-ol (100 mg, 0.42 mmol) in 5 mL of THF was added IM TBAF in THF (1.3 mL, 1.3 mmol). The reaction was stirred at rt overnight, and then was diluted with 50 mL of water and extracted with EtOAc (3×50 mL). The combined extracts were washed with brine and dried with MgSO4, filtered, and concentrated to provide 58 mg of 2-(5-ethynyl-1-methyl-1H-imidazol-2-yl)-propan-2-ol.

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d1f21687c96c4258b20c9438cd6f0c46
Source dataset
uspto-grants-2007_05
Patent number
US07214802B2

Reaction notes

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