Lithium Hydroxide → HCID 22063596, compound

HRID 1828472Notes

Reaction equation

HRID 1828472 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[N:12]=[N:11][C:10]([CH2:13][C:14]([O:16]CC)=[O:15])=[N:9]2)=[CH:5][CH:4]=1.[OH-].[Li+]>O1CCCC1.CO.O>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[N:12]=[N:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[N:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 15090418HCID 15090418, compound2×

Product 1

HCID 22063596HCID 22063596, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The ethyl 2-[2-(4-methoxybenzyl)-2H-1,2,3,4-tetrazol-5-yl]acetate (2.15 g, 7.78 mmol) obtained in (A) was dissolved in tetrahydrofuran/methanol (3:1, v/v, 60 ml), added dropwise with a solution of lithium hydroxide (359.2 mg, 8.56 mmol) in water (15 ml) under ice cooling and then stirred at room temperature for 2 hours. The solvent was evaporated, and the residue was added with 1 N aqueous hydrochloric acid to obtain pH of about 1. The solution was extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. Then, the solvent was evaporated to obtain the title compound (1.91 g, 98.8%).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was added with 1 N aqueous hydrochloric acid
  3. customto obtain pH of about 1
  4. extractionThe solution was extracted with ethyl acetate
  5. washthe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThen, the solvent was evaporated

Sources & evidence

ORD record
ord-25ab4b53c8204a019373176ac6b07ac3
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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