Lithium hydroxide, monohydrate → 2-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylic acid

HRID 528991Notes

Reaction equation

HRID 528991 reaction equation
[Br:1][C:2]1[N:3]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:4]=[C:5]([C:7]([O:9]C)=[O:8])[N:6]=1.O[Li].O>C1COCC1.CO.O>[Br:1][C:2]1[N:3]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:4]=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58638548Methyl-2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

Product 1

HCID 709813012-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylic acidYield 88%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a stirred solution of methyl 2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate (2.85 g, 8.50 mmol) in mixed solvents (THF/MeOH/water; 2:2:1; 50 mL) was added LiOH H2O (1.07 g, 25.5 mmol) at 0° C. The cold bath was removed and stirring was continued for 2 h. The reaction mixture was concentrated in vacuo, diluted with water and washed with MTBE. The aqueous layer was neutralized with 1.5N HCl and extracted with EtOAc (2×). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to provide the title compound (2.4 g, 88%) as a white solid. 1H NMR (CDCl3) δ 12.54 (br s, 1H), 8.14 (s, 1H), 5.33 (s, 2H), 3.54 (t, J=8.0 Hz, 2H), 0.85 (t, J=8.0 Hz, 2H), 0.01 (s, 9H); MS(ESI+) m/z 323.0 (M+H)+.

Workup

  1. customThe cold bath was removed
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with water
  4. washwashed with MTBE
  5. extractionextracted with EtOAc (2×)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-01419ee8b71c4431b1c9cfe23ab809bb
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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