Tetrabutylammonium Fluoride → [1-(4-fluoro-phenyl)-2-methyl-1H-imidazol-4-yl]-methanol

HRID 860145Notes

Reaction equation

HRID 860145 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[N:9]=[C:10]([CH3:20])[N:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:12]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:19][C:16]1[CH:15]=[CH:14][C:13]([N:11]2[CH:12]=[C:8]([CH2:7][OH:6])[N:9]=[C:10]2[CH3:20])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 1317261734-(tert-butyl-dimethyl-silanyloxymethyl)-1-(4-fluoro-phenyl)-2-methyl-1H-imidazole

Product 1

HCID 67303957[1-(4-fluoro-phenyl)-2-methyl-1H-imidazol-4-yl]-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(tert-Butyl-dimethyl-silanyloxymethyl)-1-(4-fluoro-phenyl)-2-methyl-1H-imidazole (14.7 g, 45.7 mmol) was dissolved in 200 mL THF. Tetrabutyl ammoniumfluoride (91 mL, 1M in THF, 91 mmol) was added and the reaction mixture was stirred at RT overnight. The solvent was evaporated. The residue was taken up in 200 mL water and extracted three times with ethyl acetate (200 mL each). The combined organic extracts were dried with magnesium sulfate, filtered and evaporated. The crude product was suspended in 150 mL ethyl acetate, filtered and dried. The desired compound was obtained as a white solid (7.16 g, 76%), MS: m/e=207.1 (M+H+).

Workup

  1. customThe solvent was evaporated
  2. extractionextracted three times with ethyl acetate (200 mL each)
  3. dry with materialThe combined organic extracts were dried with magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-d3e968249092461dad396bdee4fa2aa5
Source dataset
uspto-grants-2006_12
Patent number
US07153874B2

Reaction notes

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