Isopropyl iodide → (1-isopropyl-1H-tetrazol-5-yl)-acetic acid ethyl ester

HRID 1802787Notes

Reaction equation

HRID 1802787 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].I[CH:13]([CH3:15])[CH3:14].[OH-].[Na+].C(OC(=O)CC1N=NN(C(C)C)N=1)C>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:11])[CH2:5][C:6]1[N:10]([CH:13]([CH3:15])[CH3:14])[N:9]=[N:8][N:7]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6362Isopropyl iodideHCID 14798Sodium HydroxideHCID 543616Ethyl 1H-tetrazole-5-acetateHCID 57899268(2-isopropyl-2H-tetrazol-5-yl)-acetic acid ethyl ester

Product 1

HCID 57899300(1-isopropyl-1H-tetrazol-5-yl)-acetic acid ethyl esterYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2H-tetrazol-5-yl)-acetic acid ethyl ester (2.0 g, 13 mmol) in dimethylformamide (5 mL) was added 2-iodo-propane (11 g, 64 mmol) and sodium hydroxide (2.6 g, 64 mmol) and the solution was stirred at room temperature for 2 h. Ice water was added and the solution was extracted several times with ethyl acetate. The combined organic layers were washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified via silica gel column chromatography to provide a mixture of (2-isopropyl-2H-tetrazol-5-yl)-acetic acid ethyl ester and (1-isopropyl-1H-tetrazol-5-yl)-acetic acid ethyl ester (2 g, 79% yield).

Workup

  1. extractionthe solution was extracted several times with ethyl acetate
  2. washThe combined organic layers were washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified via silica gel column chromatography
  7. customto provide

Sources & evidence

ORD record
ord-b295629c86704eb091247f3d12385da8
Source dataset
uspto-grants-2013_01
Patent number
US08349883B2

Reaction notes

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