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

HRID 1009736Notes

Reaction equation

HRID 1009736 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 room temperature 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-70bf59a60d9b4fe084304d2d85ee4984
Source dataset
uspto-grants-2011_07
Patent number
US07973165B2

Reaction notes

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