Tetrabutylammonium Fluoride → (1-Methyl-2-phenyl-1H-imidazol-4-yl)methanol

HRID 1397431Notes

Reaction equation

HRID 1397431 reaction equation
[Si]([O:18][CH2:19][C:20]1[N:21]=[C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:23]([CH3:25])[CH:24]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:25][N:23]1[CH:24]=[C:20]([CH2:19][OH:18])[N:21]=[C:22]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67324865HCID 67324865, compound

Product 1

HCID 13553457(1-Methyl-2-phenyl-1H-imidazol-4-yl)methanolYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(((tert-butyldiphenylsilyl)oxy)methyl)-1-methyl-2-phenyl-1H-imidazole (1.25 g, 2.93 mmol) in dry THF (25 mL) was cooled to 0° C. and tetrabutylammonium fluoride (5.9 mL, 5.86 mmol, 1M in THF) was added dropwise. The reaction mixture was allowed to warm up to room temperature and further stirred for 3 h. The reaction mixture was quenched with brine and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluant 2-4% MeOH in CH2Cl2) to get (1-methyl-2-phenyl-1H-imidazol-4-yl)methanol (0.26 mg, yield 47%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.68-7.66 (m, 2H), 7.50-7.41 (m, 3H), 7.11 (s, 1H), 4.92 (br s, 1H), 4.37 (s, 2H), 3.71 (s, 3H). MS (ESI) m/z: Calculated for C11H12N2O: 188.09. found: 188.9 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with brine
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (silica 60-120 mesh, eluant 2-4% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-36e07aa6bd4745e3bac3f45584c52057
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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