Methyl iodide → 3-(2-methyl-2H-tetrazol-5-yl)-phenol

HRID 2081088Notes

Reaction equation

HRID 2081088 reaction equation
[C:1](=O)([O-])[O-].[Cs+].[Cs+].[N:7]1[NH:8][N:9]=[N:10][C:11]=1[C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1.IC>O1CCCC1.CN(C)C=O>[CH3:1][N:9]1[N:8]=[N:7][C:11]([C:12]2[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=2)=[N:10]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 134557633-(2H-Tetrazol-5-yl)phenol

Product 1

HCID 536765503-(2-methyl-2H-tetrazol-5-yl)-phenol

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of cesium carbonate (0.60 g, 1.83 mmol), 3-(2H-tetrazol-5-yl)-phenol (0.30 g, 1.85 mmol) (from Example 25 supra) in tetrahydrofuran-N,N-dimethylformamide (5:2, 17.5 mL) was heated at 70° C. for 3 hours. Iodomethane (0.29 g, 2.04 mmol) (Aldrich) was added. Heating was continued for 18 hours. The reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate (2×). The combined organic phase washed with water and brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography eluting with 40% ethyl acetate in hexanes to give 3-(2-methyl-2H-tetrazol-5-yl)-phenol. (Yield 0.23 g, 70%).

Workup

  1. temperatureHeating
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×)
  4. washThe combined organic phase washed with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography
  8. washeluting with 40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-73d9fe97df084190b1e238e81d32c1a3
Source dataset
uspto-grants-2011_04
Patent number
US07932390B2

Reaction notes

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