Tetrabutylammonium Fluoride → 1-(3-Hydroxymethyl-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester

HRID 547588Notes

Reaction equation

HRID 547588 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17](C)(C)[O:18][SiH2]C(C)(C)C)[CH:12]=2)[CH:10]=1)=[O:5])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][OH:18])[CH:12]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131728825Ethyl 1-[3-(2-tert-butylsilyloxypropan-2-yl)phenyl]imidazole-4-carboxylate

Product 1

HCID 578263591-(3-Hydroxymethyl-phenyl)-1H-imidazole-4-carboxylic acid ethyl esterYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of compound 6 (1.50 g, 4.2 mmol) in THF (18 mL) was added tetrabutylammonium fluoride (1.58 g, 5 mmol) and refluxed at 70° C. for 12 h. After concentration, the residue was purified by filter column using 4% methanol in chloroform to give alcohol 7 (810 mg, 79%) as pale yellow gum.

Workup

  1. concentrationAfter concentration
  2. customthe residue was purified
  3. filtrationby filter column

Sources & evidence

ORD record
ord-a50b76c2934e40d985d86d1abf72369b
Source dataset
uspto-grants-2011_05
Patent number
US07939556B2

Reaction notes

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