Sulfuric Acid → Ethyl (2-tert-butyl-2H-tetrazol-5-yl)acetate

HRID 549417Notes

Reaction equation

HRID 549417 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH2:5][C:6]1[N:7]=[N:8][NH:9][N:10]=1)[CH3:2].S(=O)(=O)(O)O.C(OCC)(=O)C.[OH-].[Na+].[CH3:25][C:26](O)([CH3:28])[CH3:27]>FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4](=[O:11])[CH2:5][C:6]1[N:7]=[N:8][N:9]([C:26]([CH3:28])([CH3:27])[CH3:25])[N:10]=1)[CH3:2]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 543616Ethyl 1H-tetrazole-5-acetate

Product 1

HCID 13142201Ethyl (2-tert-butyl-2H-tetrazol-5-yl)acetateYield 52%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of (2H-tetrazol-5-yl)-acetic acid ethyl ester (2.0 g, 13 mmol) in 2-methyl-propan-2-ol (2.6 mL) and trifluoroacetic acid (6 mL) was added concentrated sulfuric acid (0.35 mL, 6.4 mmol) and the reaction was stirred at room temperature for 12 h. Ethyl acetate was added and the solution was neutralized by addition of an aqueous sodium hydroxide solution (2 N). The solution was extracted several times with ethyl acetate, and the organic layers were combined, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel column chromatography to provide (2-tert-butyl-2H-tetrazol-5-yl)-acetic acid ethyl ester (2.0 g, 52% yield).

Workup

  1. extractionThe solution was extracted several times with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-15be93b330484d73ab50446c211b70d4
Source dataset
uspto-grants-2011_05
Patent number
US07943652B2

Reaction notes

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