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

HRID 2109203Notes

Reaction equation

HRID 2109203 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 21097252HCID 21097252, compound

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 1M 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-31531bb6de4c4beb9993a9e673cbcd81
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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